UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549

                                    FORM 10-K

 [X] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE
     ACT OF 1934

                   For the fiscal year ended December 31, 1999

                         WINTRUST FINANCIAL CORPORATION
             (Exact name of registrant as specified in its charter)

                                     0-21923
                             Commission File Number

                 ILLINOIS                                 36-3873352
(State of incorporation or organization)    (I.R.S. Employer Identification No.)

                               727 NORTH BANK LANE
                           LAKE FOREST, ILLINOIS 60045
                    (Address of principal executive offices)

                                 (847) 615-4096
              (Registrant's telephone number, including area code)

                           COMMON STOCK, NO PAR VALUE
           Securities registered pursuant to Section 12(g) of the Act

Indicate  by check  mark  whether  the  registrant:  (1) has filed  all  reports
required to be filed by Section 13 or 15(d) of the  Securities  Exchange  Act of
1934  during  the  preceding  12 months  (or for such  shorter  period  that the
registrant was required to file such reports),  and (2) has been subject to such
filing requirements for the past 90 days. Yes  X  No
                                              ---    ---

Indicate by check mark if disclosure of delinquent  filers  pursuant to Item 405
of Regulation  S-K is not contained  herein,  and will not be contained,  to the
best  of  the  registrant's   knowledge,  in  definitive  proxy  or  information
statements  incorporated  by  reference  in Part  III of this  Form  10-K or any
amendment to this Form 10-K. [ ]

The  aggregate  market value of the voting stock held by  non-affiliates  of the
registrant was approximately  $110,190,000 as of March 23, 2000. As of March 23,
2000, the registrant had outstanding 8,752,643 shares of Common Stock.

                       DOCUMENTS INCORPORATED BY REFERENCE

Portions of the Annual Report to  Shareholders  for the year ended  December 31,
1999,  which is included as Exhibit 13.1 to this Form 10-K, are  incorporated by
reference into Parts I and II hereof and portions of the Proxy Statement for the
Company's  Annual  Meeting  of  Shareholders  to be  held on May  25,  2000  are
incorporated by reference into Part III.


                                TABLE OF CONTENTS

                                     PART I

                                                                            Page
                                                                            ----
ITEM 1.   Business.......................................................     3

ITEM 2.   Properties.....................................................    16

ITEM 3.   Legal Proceedings..............................................    18

ITEM 4.   Submission of Matters to a Vote of Security Holders............    18

                                     PART II

ITEM 5.   Market for Registrant's Common Equity and Related
               Stockholder Matters.......................................    18

ITEM 6.   Selected Financial Data........................................    19

ITEM 7.   Management's Discussion and  Analysis of Financial Condition
               and Results of Operations.................................    20

ITEM 7A.  Quantitative and Qualitative Disclosures About Market Risks....    20

ITEM 8.   Financial Statements and Supplementary Data....................    20

ITEM 9.   Changes in and Disagreements with Accountants on Accounting
               and Financial Disclosure..................................    27

                                    PART III

ITEM 10.  Directors and Executive Officers of the Registrant.............    27

ITEM 11.  Executive Compensation.........................................    27

ITEM 12.  Security Ownership of Certain Beneficial Owners and Management.    27

ITEM 13.  Certain Relationships and Related Transactions.................    27

                                     PART IV

ITEM 14.  Exhibits, Financial Statement Schedules and Reports on Form 8-K.   28

          Signatures......................................................   33


                                     - 2 -

                                     PART I

ITEM 1. BUSINESS

Wintrust Financial  Corporation,  an Illinois corporation (the "Company"),  is a
bank  holding  company  based in Lake  Forest,  Illinois,  with total  assets of
approximately  $1.7  billion at December  31,  1999.  The  Company is  currently
engaged in the  business of  providing  community  banking  services,  trust and
investment services, commercial insurance premium financing, short-term accounts
receivable  financing,   and  certain  administrative  services,  such  as  data
processing of payrolls, billing and cash management services.

The  Company  provides  community-oriented,   personal  and  commercial  banking
services to  customers  located  predominantly  in affluent  suburbs of Chicago,
Illinois  through  its  six  wholly-owned  banking  subsidiaries  (collectively,
"Banks"),  all of which  started as de novo (i.e.,  started  new)  institutions,
including Lake Forest Bank and Trust Company ("Lake Forest Bank"), Hinsdale Bank
and Trust  Company  ("Hinsdale  Bank"),  North  Shore  Community  Bank and Trust
Company ("North Shore Bank"), Libertyville Bank and Trust Company ("Libertyville
Bank"),  Barrington Bank and Trust Company, N.A. ("Barrington Bank") and Crystal
Lake Bank & Trust Company,  N.A.  ("Crystal Lake Bank").  Through Hinsdale Bank,
the Company  operates its  indirect  auto  segment,  which is in the business of
providing  new  and  used  automobile  loans  through  a large  network  of auto
dealerships  within the  Chicago  metropolitan  area.  All  indirect  auto loans
originated  are  currently   being  retained  within  each  of  the  Banks' loan
portfolios.

On September 30, 1998, the Company began providing trust and investment services
at each  of its  Banks  through  its  wholly-owned  subsidiary,  Wintrust  Asset
Management  Company,  N.A.  ("WAMC").  Previously,  the Company  provided  trust
services  through the trust department of Lake Forest Bank. The Company provides
financing for the payment of commercial  insurance  premiums  ("premium  finance
receivables"),  on a national basis, through First Insurance Funding Corporation
("FIFC"), a wholly-owned subsidiary of Crabtree Capital Corporation ("Crabtree")
which is a  wholly-owned  subsidiary  of Lake Forest Bank.  On October 26, 1999,
Hinsdale  Bank  acquired  Tricom,  Inc. of Milwaukee  ("Tricom"),  a provider of
short-term  accounts  receivable  financing  ("Tricom finance  receivables") and
value-added  out-sourced  administrative  services,  such as data  processing of
payrolls,  billing and cash management  services,  to temporary staffing service
clients located throughout the United States.

As a mid-size  financial  services company,  management  expects to benefit from
greater  access to financial and  managerial  resources  while  maintaining  its
commitment to localized decision-making and to its community banking philosophy.
Management  also believes the Company is positioned to compete more  effectively
with other larger and more diversified  banks,  bank holding companies and other
financial  services  companies  as it  continues  its  growth  strategy  through
additional  branch openings and de novo bank formations,  expansion of trust and
investment activities, pursuit of specialized earning asset niches and potential
acquisitions of banks or specialty finance companies.


                                     - 3 -

Additional  information  regarding  the  Company's  business and  strategies  is
included in the 1999 Annual  Report to  Shareholders,  which is filed as Exhibit
13.1 to this Form 10-K. Such information is incorporated herein by reference and
constitutes a part of this report.

BANKING
- -------

The Company  provides  banking and  financial  services  to  individuals,  small
businesses,   local  governmental  units  and  institutional   clients  residing
primarily in the Banks' local service areas. These services include  traditional
demand,  NOW,  money  market,  savings and time deposit  accounts,  as well as a
number of unique deposit  products  targeted to specific  market  segments.  The
Banks offer home equity,  home  mortgage,  consumer,  real estate and commercial
loans,  safe deposit  facilities,  ATMs, and other  innovative  and  traditional
services  specially  tailored  to meet the needs of  customers  in their  market
areas.  The Hinsdale Bank also operates the indirect auto segment which provides
high quality new and used auto loans through a large network of auto dealerships
within the Chicago  metropolitan  area.  All indirect  auto loans are  currently
being purchased by the Banks and retained within their loan portfolios.

Each of the Banks was founded as a de novo banking  organization within the last
nine  years.  The  organizational  efforts  began  in  1991,  when  a  group  of
experienced  bankers and local business  people  identified an unfilled niche in
the Chicago  metropolitan  area retail banking  market.  As large banks acquired
smaller ones and personal service was subjected to consolidation strategies, the
opportunity increased in affluent suburbs for locally owned and operated, highly
personal  service-oriented  banks. As a result,  Lake Forest Bank was founded in
December  1991 to service  the Lake  Forest and Lake Bluff  communities.  A Lake
Bluff branch of this bank was opened in 1994. In 1993,  Hinsdale Bank was opened
to service the communities of Hinsdale and Burr Ridge. Hinsdale Bank established
branch  facilities  in  Clarendon  Hills and  Western  Springs in 1996 and 1997,
respectively. In 1994, North Shore Bank was started in order to service Wilmette
and Kenilworth. North Shore Bank opened branch facilities in Glencoe during 1995
and 1998, in Winnetka  during 1996 to service  Winnetka and  Northfield,  and in
Skokie  during  1999.  In  1995,   Libertyville   Bank  was  opened  to  service
Libertyville,  Vernon  Hills and  Mundelein.  Libertyville  Bank opened a branch
facility in south  Libertyville  during 1998 to service south  Libertyville  and
Vernon  Hills.  In  December  1996,  Barrington  Bank was opened to service  the
greater  Barrington/Inverness  areas.  In December  1997,  Crystal Lake Bank was
opened to serve the Crystal Lake/Cary  communities.  In 1999,  Crystal Lake Bank
opened two new branch  facilities in Crystal Lake.  All Banks are insured by the
Federal  Deposit  Insurance  Company  ("FDIC")  and are  subject to  regulation,
supervision  and regular  examination  by the Illinois  Office of Banks and Real
Estate,  the  Federal  Reserve  Bank  and/or  the Office of the  Comptroller  of
Currency ("OCC").

PREMIUM FINANCE
- ---------------

FIFC  commenced  operations  nine years ago and is  headquartered  in Deerfield,
Illinois.  Based on limited  industry data available in certain state regulatory
filings and FIFC management's experience in and knowledge of the premium finance
industry,  management estimates that, ranked by origination volumes, FIFC is one
of the top five  premium  finance  companies  operating  in the  United  States.
Premium finance  receivables  are originated by FIFC's own sales force,  working
with medium and large insurance agents and brokers throughout the United States.
These  receivables are retained

                                     - 4 -

mainly within the Banks' loan  portfolios  and are also sold to an  unaffiliated
financial institution.  Insurance premiums are financed primarily for commercial
customers' purchase of property, casualty and liability insurance. Substantially
all  premium  finance  receivables  are  made to  commercial  accounts.  FIFC is
licensed or otherwise  qualified to do business as an insurance  premium finance
company in all 50 states and the District of Columbia.

TRUST ACTIVITIES
- ----------------

With the formation of WAMC in September  1998, the Company intends to expand the
trust and investment  management  services  previously  provided through a trust
department  of the Lake Forest Bank.  As a separately  chartered  non-depository
bank  subsidiary,  the  Company  is better  able to offer  trust and  investment
management services to all of the Banks' communities,  which management believes
are some of the best trust  markets in Illinois.  In addition to offering  these
services to existing bank customers at each of the Banks, WAMC intends to target
small to mid-size businesses and newly affluent  individuals whose needs command
the  personalized  attention  that will be offered  by WAMC and its  experienced
trust  professionals.  Services  offered  typically  include  traditional  trust
products and services, as well as investment management,  financial planning and
401(k)  management  services.  WAMC is subject to  regulation,  supervision  and
regular examination by the OCC.

TRICOM
- ------

On October 26, 1999  (effective  as of October 1, 1999),  Hinsdale Bank acquired
100% of the common stock of Tricom. This acquisition is another significant step
in the Company's strategy to pursue specialized earning asset niches.  Tricom is
a Milwaukee-based  company that has been in business for approximately ten years
and  specializes  in  providing,   on  a  national  basis,  short-term  accounts
receivable financing and value-added out-sourced  administrative  services, such
as data processing of payrolls, billing and cash management services, to clients
in the  temporary  staffing  industry.  On an  annual  basis,  Tricom  currently
finances  and  processes  payrolls  with  associated  billings in excess of $200
million and  generates  approximately  $7 million in revenues.  By virtue of the
Company's  funding   resources,   this  acquisition  will  provide  Tricom  with
additional  capital  necessary  to expand its  financing  services in a national
market.  In addition to expanding  the  Company's  earning  asset  niches,  this
acquisition  will  add  to  the  level  of  fee-based  income  and  augment  its
community-based banking revenues.

COMPETITION
- -----------

The Company competes in the commercial banking industry through the Banks in the
communities each serves. The commercial banking industry is highly  competitive,
and the Banks face strong  direct  competition  for deposits,  loans,  and other
financial-related services. The Banks compete directly in Cook, DuPage, Lake and
McHenry  counties  with  other  commercial   banks,   thrifts,   credit  unions,
stockbrokers,  and the finance divisions of automobile companies.  Some of these
competitors are local, while others are statewide or nationwide.  The Banks have
developed  a community  banking and  marketing  strategy.  In keeping  with this
strategy,  the Banks provide  highly  personalized  and  responsive  service,  a
characteristic  of locally-owned  and managed  institutions.  As such, the Banks
compete for  deposits  principally  by offering  depositors a variety of deposit
programs,  convenient office locations,  hours and other services,  and for loan
originations primarily through the interest

                                     - 5 -

rates and loan fees they charge,  the  efficiency  and quality of services  they
provide  to  borrowers  and the  variety  of their  loan  products.  Some of the
financial institutions and financial services organizations with which the Banks
compete  are not  subject to the same  degree of  regulation  as imposed on bank
holding   companies,   Illinois   banking   corporations  and  national  banking
associations.  In addition,  the larger banking organizations have significantly
greater resources than are available to the Banks. As a result, such competitors
have advantages over the Banks in providing certain non-deposit services.

FIFC  encounters  intense  competition  from numerous  other firms,  including a
number of national  commercial premium finance companies,  companies  affiliated
with insurance carriers, independent insurance brokers who offer premium finance
services,  banks and other lending institutions.  Some of FIFC's competitors are
larger and have greater  financial and other resources and are better known than
FIFC. FIFC competes with these entities by emphasizing a high level of knowledge
of the insurance industry,  flexibility in structuring  financing  transactions,
and the  timely  purchase  of  qualifying  contracts.  FIFC  believes  that  its
commitment to account service also distinguishes it from its competitors.  It is
FIFC's policy to notify the insurance agent when an insured is in default and to
assist in collection,  if requested by the agent.  To the extent that affiliates
of insurance carriers, banks, and other lending institutions add greater service
and  flexibility  to their  financing  practices  in the future,  the  Company's
operations could be adversely affected. There can be no assurance that FIFC will
be able to continue to compete successfully in its markets.

WAMC's primary  competition is with more  established  trust  companies of other
larger bank  holding  companies.  WAMC is also in  competition  with other trust
companies,  brokerage and other financial  service  companies,  stockbrokers and
financial  advisors.  As a new company, it may be more difficult to successfully
attract new customers than the more  established  Chicago area trust  companies.
However,  the Company believes it can successfully compete for trust business by
offering  personalized  attention  and  customer  service  to small to  mid-size
businesses and newly  affluent  individuals.  The hiring of several  experienced
trust  professionals  from the more established  Chicago area trust companies is
also expected to help in attracting new customer relationships.  There can be no
assurances,  however,  that WAMC will be  successful  in  establishing  this new
business as a preferred  alternative  to the larger  trust  companies,  and as a
profitable venture.

Tricom  competes with numerous other firms,  including a small number of similar
niche finance companies and payroll processing firms, as well as various finance
companies, banks and other lending institutions. Tricom management believes that
its commitment to service  distinguishes itself from competitors.  To the extent
that other finance  companies,  financial  institutions  and payroll  processing
firms add greater programs and services to their existing  businesses,  Tricom's
operations  could be adversely  affected.  There can be no assurance that Tricom
will be able to continue to compete successfully in its markets.

EMPLOYEES
- ---------

At December 31, 1999, the Company and its  subsidiaries  employed a total of 412
full-time-equivalent   employees.   The  Company  provides  its  employees  with
comprehensive  medical and dental benefit plans,  life insurance  plans,  401(k)
plans  and  an  employee  stock   purchase  plan.  The  Company   considers  its
relationship with its employees to be good.

                                     - 6 -

FORWARD-LOOKING STATEMENTS
- --------------------------

This document contains forward-looking  statements within the meaning of Section
27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act
of 1934. The Company  intends such  forward-looking  statements to be covered by
the safe harbor  provisions  for  forward-looking  statements  contained  in the
Private  Securities  Litigation  Reform  Act  of  1995,  and is  including  this
statement  for  purposes  of  invoking  these  safe  harbor   provisions.   Such
forward-looking  statements  may be  deemed  to  include,  among  other  things,
statements relating to the Company's projected growth,  anticipated improvements
in earnings,  earnings per share and other financial performance  measures,  and
management's  long-term performance goals, as well as statements relating to the
anticipated effects on financial results of condition from expected  development
or events, the Company's business and growth strategies,  including  anticipated
internal  growth,  plans to form additional de novo banks and to open new branch
offices, and to pursue additional potential  development or acquisition of banks
or specialty  finance  businesses.  Actual results could differ  materially from
those  addressed  in the  forward-looking  statements  as a result  of  numerous
factors, including the following:

o    The level of reported  net income,  return on average  assets and return on
     average  equity  for the  Company  will in the  near  term  continue  to be
     impacted by start-up costs associated with de novo bank formations,  branch
     openings, and expanded trust and investment  operations.  De novo banks may
     typically require 13 to 24 months of operations before becoming profitable,
     due to the impact of  organizational  and overhead  expenses,  the start-up
     phase  of  generating  deposits  and the  time lag  typically  involved  in
     redeploying  deposits  into  attractively  priced  loans and  other  higher
     yielding earning assets.  Similarly,  the expansion of trust and investment
     services through the Company's newer trust subsidiary, WAMC, is expected to
     be in a start-up phase for the next few years, before becoming profitable.

o    The  Company's  success to date has been and will  continue  to be strongly
     influenced  by  its  ability  to  attract  and  retain  senior   management
     experienced in banking and financial services.

o    Although  management  believes the  allowance  for possible  loan losses is
     adequate to absorb  losses that may develop in the  existing  portfolio  of
     loans and leases,  there can be no assurance  that the allowance will prove
     sufficient to cover actual future loan or lease losses.

o    If market interest rates should move contrary to the Company's gap position
     on interest earning assets and interest bearing liabilities, the "gap" will
     work  against  the Company and its net  interest  income may be  negatively
     affected.

o    The financial  services business is highly competitive which may affect the
     pricing of the Company's loan and deposit products as well as its services.

o    The Company's  ability to adapt  successfully to  technological  changes to
     compete effectively in the marketplace.

                                     - 7 -

o    The extent of the Company's  preparedness  efforts, and that of its outside
     data processing providers, software vendors, and customers, in implementing
     and testing Year 2000  compliant  hardware,  software and systems,  and the
     effectiveness of appropriate contingency plans that have been developed.

o    Unforeseen future events that may cause slower than anticipated development
     and  growth of the  Tricom  business,  changes  in the  temporary  staffing
     industry or difficulties integrating the Tricom acquisition.

o    Changes in the economic  environment,  competition,  or other factors,  may
     influence the anticipated growth rate of loans and deposits, the quality of
     the loan portfolio and loan and deposit pricing.

SUPERVISION AND REGULATION
- --------------------------

Bank holding  companies and banks are  extensively  regulated  under federal and
state law.  References under this heading to applicable  statutes or regulations
are brief summaries or portions  thereof which do not purport to be complete and
which are  qualified  in their  entirety  by  reference  to those  statutes  and
regulations.  Any change in applicable  laws or regulations  may have a material
adverse effect on the business of commercial  banks and bank holding  companies,
including the Company, the Banks, FIFC, WAMC and Tricom. However,  management is
not aware of any current  recommendations by any regulatory  authority which, if
implemented,  would have or would be reasonably likely to have a material effect
on liquidity,  capital resources, or operations of the Company, the Banks, FIFC,
WAMC or Tricom.

BANK HOLDING COMPANY REGULATION

The Company is registered as a "bank holding  company" with the Federal  Reserve
and,  accordingly,  is subject to supervision  by the Federal  Reserve under the
Bank  Holding  Company Act (the Bank  Holding  Company  Act and the  regulations
issued  thereunder,  are collectively the "BHC Act"). The Company is required to
file with the Federal Reserve periodic  reports and such additional  information
as the Federal Reserve may require  pursuant to the BHC Act. The Federal Reserve
examines the Company and may examine the Banks, FIFC, WAMC or Tricom.

The BHC Act requires prior Federal Reserve approval for, among other things, the
acquisition by a bank holding company of direct or indirect ownership or control
of more than five percent of the voting shares or  substantially  all the assets
of any bank or bank holding company,  or for a merger or consolidation of a bank
holding company with another bank holding company. With certain exceptions,  the
BHC Act  prohibits a bank  holding  company  from  acquiring  direct or indirect
ownership or control of voting shares of any company which is not a bank or bank
holding  company and from engaging  directly or indirectly in any activity other
than banking or managing or  controlling  banks or  performing  services for its
authorized  subsidiaries.  A bank  holding  company may,  however,  engage in or
acquire an interest in a company  that engages in  activities  which the Federal
Reserve has  determined,  by  regulation or order,  to be so closely  related to
banking or managing or  controlling  banks as to be a proper  incident  thereto,
such as owning and operating the

                                     - 8 -

premium  finance  business  conducted  by FIFC.  Under  the BHC Act and  Federal
Reserve  regulations,  the Company and the Banks are prohibited from engaging in
certain tie-in  arrangements in connection  with an extension of credit,  lease,
sale of property, or furnishing of services.

Any person,  including associates and affiliates of and groups acting in concert
with such person,  who purchases or  subscribes  for five percent or more of the
Company's  Common Stock may be required to obtain prior approval of the Illinois
Commissioner and the Federal Reserve. Under the Illinois Banking Act, any person
who thereafter  acquires stock of the Company such that its interest exceeds ten
percent of the  Company,  may be  required  to obtain the prior  approval of the
Illinois  Commissioner and under the Change in Bank Control Act, a person may be
required to obtain the prior regulatory approval of the FDIC or OCC, in the case
of Barrington Bank,  Crystal Lake Bank, and WAMC, and the Federal Reserve before
acquiring the power to directly or indirectly direct the management,  operations
or  policies  of the  Company  or the Banks or before  acquiring  control  of 25
percent  or more of any  class of the  Company's  or Banks'  outstanding  voting
stock.  In addition,  any Company,  partnership,  trust or organized  group that
acquires a  controlling  interest in the Company or the Banks may have to obtain
approval of the Federal  Reserve to become a bank holding company and thereafter
be subject to regulation as such.

It is the policy of the Federal Reserve that the Company is expected to act as a
source of financial  strength to the Banks and WAMC, and to commit  resources to
support  the Banks and WAMC.  The Federal  Reserve  takes the  position  that in
implementing  this  policy,  it may require the Company to provide  such support
when the Company otherwise would not consider itself able to do so.

The Federal  Reserve has  risk-based  capital  requirements  for assessing  bank
holding company capital adequacy.  These standards define regulatory capital and
establish  minimum capital standards in relation to assets and off-balance sheet
exposures,  as adjusted for credit risks. Under the Federal Reserve's risk-based
guidelines,  capital  is  classified  into  two  categories.  For  bank  holding
companies,  Tier 1 or "core" capital  consists of common  shareholders'  equity,
perpetual  preferred and trust preferred stock (subject to certain  limitations)
and  minority   interests  in  the  common  equity   accounts  of   consolidated
subsidiaries,  and is reduced by goodwill,  certain other intangible  assets and
certain  investments  in other  companies  ("Tier 1  Capital").  Tier 2  capital
consists  of the  allowance  for loan  and  lease  losses  (subject  to  certain
conditions and  limitations),  perpetual  preferred and trust  preferred  stock,
"hybrid  capital  instruments,"  perpetual debt and mandatory  convertible  debt
securities, and term subordinated debt and intermediate-term preferred stock.

Under the Federal  Reserve's  capital  guidelines,  bank holding  companies  are
required  to maintain a minimum  ratio of  qualifying  capital to  risk-weighted
assets of 8.0%,  of which at least  4.0% must be in the form of Tier 1  Capital.
The Federal Reserve also requires a minimum  leverage ratio of Tier 1 Capital to
total  assets of 3.0%,  except  that  bank  holding  companies  not rated in the
highest  category under the regulatory  rating system are required to maintain a
leverage  ratio of 1.0% to 2.0% above such  minimum.  The 3.0% Tier 1 Capital to
total assets ratio  constitutes the minimum  leverage  standard for bank holding
companies,  and  will  be used in  conjunction  with  the  risk-based  ratio  in
determining the overall capital adequacy of banking organizations.  In addition,
the  Federal  Reserve  continues  to  consider  the  Tier 1  leverage  ratio  in
evaluating proposals for expansion or new activities.

                                     - 9 -

In its capital  adequacy  guidelines,  the Federal  Reserve  emphasizes that the
foregoing  standards  are  supervisory  minimums and that banking  organizations
generally  are  expected  to  operate  well  above  the  minimum  ratios.  These
guidelines also provide that banking organizations  experiencing internal growth
or making  acquisitions  will be expected to maintain  strong capital  positions
substantially above the minimum levels.

BANK REGULATION

Under Illinois law, each of Lake Forest Bank,  Hinsdale Bank,  North Shore Bank,
Libertyville  Bank and  their  subsidiaries,  are  subject  to  supervision  and
examination by the Illinois  Commissioner.  As an affiliate of these Banks,  the
Company is also subject to examination by the Illinois Commissioner.  Barrington
Bank,  Crystal Lake Bank and WAMC are subject to supervision  and examination by
the  OCC  pursuant  to  the  National  Bank  Act  and  regulations   promulgated
thereunder.  Each of the Banks and WAMC are members of the Federal  Reserve Bank
and, as such, is also subject to examination by the Federal Reserve.

The  deposits  of the Banks are  insured  by the Bank  Insurance  Fund under the
provisions of the Federal Deposit Insurance Act (the "FDIA"), and the Banks are,
therefore,  also subject to  supervision  and  examination by the FDIC. The FDIC
requires that the appropriate federal regulatory  authority (the Federal Reserve
Bank and/or the FDIC in the case of Lake Forest Bank, North Shore Bank, Hinsdale
Bank and  Libertyville  Bank,  or the OCC,  in the case of  Barrington  Bank and
Crystal Lake Bank) approve any merger and/or consolidation by or with an insured
bank, as well as the  establishment  or relocation of any bank or branch office.
The FDIC also  supervises  compliance  with the  provisions  of federal  law and
regulations  which place  restrictions on loans by  FDIC-insured  banks to their
directors, executive officers and other controlling persons.

Furthermore,  banks  are  affected  by the  credit  policies  of other  monetary
authorities,  including the Federal Reserve,  which regulate the national supply
of bank  credit.  Such  regulation  influences  overall  growth  of bank  loans,
investments,  and deposits and may also affect  interest  rates charged on loans
and paid on deposits.  The monetary  policies of the Federal  Reserve have had a
significant  effect on the operating results of commercial banks in the past and
are expected to continue to do so in the future.

FINANCIAL INSTITUTION REGULATION GENERALLY

Transactions  with  Affiliates.  Transactions  between  a bank  and its  holding
company or other affiliates are subject to various restrictions imposed by state
and federal  regulatory  agencies.  Such  transactions  include  loans and other
extensions of credit,  purchases of securities and other assets, and payments of
fees or other distributions.  In general, these restrictions limit the amount of
transactions  between an institution  and an affiliate of such  institution,  as
well as the aggregate  amount of transactions  between an institution and all of
its  affiliates,  and  require  transactions  with  affiliates  to be  on  terms
comparable to those for transactions with unaffiliated entities.

                                     - 10 -

Dividend  Limitations.  As a holding company, the Company is primarily dependent
upon  dividend  distributions  from its operating  subsidiaries  for its income.
Federal and state statutes and regulations impose restrictions on the payment of
dividends  by the Company,  the Banks and WAMC.  See Part II, Item 5 for further
discussion of dividend limitations.

Federal  Reserve  policy  provides  that a bank holding  company  should not pay
dividends  unless (i) the bank holding  company's net income over the prior year
is  sufficient  to fully fund the  dividends  and (ii) the  prospective  rate of
earnings  retention appears consistent with the capital needs, asset quality and
overall financial condition of the bank holding company and its subsidiaries.

Illinois law also places  certain  limitations  on the ability of the Company to
pay  dividends.   For  example,  the  Company  may  not  pay  dividends  to  its
shareholders  if, after giving effect to the dividend,  the Company would not be
able to pay its debts as they become due. Since a major potential  source of the
Company's  funding is dividends  the Company  expects to receive from the Banks,
the  Company's  ability to pay dividends is likely to be dependent on the amount
of dividends  paid by the Banks.  No assurance can be given that the Banks will,
in any circumstances, pay dividends to the Company.

As Illinois  state-chartered  banks, none of Lake Forest Bank, North Shore Bank,
Hinsdale Bank nor Libertyville  Bank may pay dividends in an amount greater than
its current net profits  after  deducting  losses and bad debts out of undivided
profits provided that its surplus equals or exceeds its capital. For the purpose
of determining  the amount of dividends that an Illinois bank may pay, bad debts
are defined as debts upon which  interest is past due and unpaid for a period of
six months or more  unless  such debts are  well-secured  and in the  process of
collection.  Furthermore,  federal regulations also prohibit any Federal Reserve
member bank,  including each of the Banks and WAMC, from declaring  dividends in
any calendar year in excess of its net profit for the year plus the retained net
profits  for the  preceding  two years.  Similarly,  as  national  associations,
Barrington  Bank,  Crystal  Lake Bank and WAMC may not declare  dividends in any
year in excess of its net profit for the year plus the  retained net profits for
the preceding two years. Furthermore,  the OCC may, after notice and opportunity
for  hearing,  prohibit  the  payment  of a dividend  by a  national  bank if it
determines that such payment would constitute an unsafe or unsound practice.

In addition to the foregoing,  the ability of the Company, the Banks and WAMC to
pay dividends may be affected by the various  minimum capital  requirements  and
the capital and  non-capital  standards  established  under the Federal  Deposit
Insurance Company  Improvements Act of 1991 ("FDICIA"),  as described below. The
right of the Company,  its  shareholders and its creditors to participate in any
distribution of the assets or earnings of its subsidiaries is further subject to
the prior claims of creditors of the respective subsidiaries.

Standards  for  Safety  and  Soundness.  The FDIA,  as amended by FDICIA and the
Riegle Community Development and Regulatory Improvement Act of 1994 requires the
Federal Reserve,  together with the other federal bank regulatory  agencies,  to
prescribe  standards of safety and  soundness,  by  regulations  or  guidelines,
relating  generally to operations and management,  asset growth,  asset quality,
earnings,  stock valuation,  and compensation.  The Federal Reserve, the OCC and
the federal bank regulatory  agencies have adopted,  effective August 9, 1995, a
set of guidelines prescribing safety and soundness standards pursuant to FDICIA,
as amended.  The guidelines  establish  general  standards  relating to internal
controls and information systems, internal audit systems, loan

                                     - 11 -

documentation,  credit underwriting,  interest rate exposure,  asset growth, and
compensation, fees and benefits. In general, the guidelines require, among other
things,  appropriate  systems and practices to identify and manage the risks and
exposures  specified  in  the  guidelines.  The  guidelines  prohibit  excessive
compensation  as an unsafe and unsound  practice  and describe  compensation  as
excessive  when the amounts paid are  unreasonable  or  disproportionate  to the
services  performed by an  executive  officer,  employee,  director or principal
shareholder.  In  addition,  each of the  Federal  Reserve  and the OCC  adopted
regulations that authorize,  but do not require, the Federal Reserve or the OCC,
as the case may be, to order an  institution  that has been given  notice by the
Federal Reserve or the OCC, as the case may be, that it is not satisfying any of
such safety and soundness standards to submit a compliance plan. If, after being
so notified,  an institution  fails to submit an acceptable  compliance  plan or
fails in any  material  respect to implement an accepted  compliance  plan,  the
Federal  Reserve or the OCC, as the case may be,  must issue an order  directing
action to correct the deficiency and may issue an order  directing other actions
of the  types to which an  undercapitalized  association  is  subject  under the
"prompt  corrective  action"  provisions of FDICIA.  If an institution  fails to
comply with such an order,  the Federal  Reserve or the OCC, as the case may be,
may seek to enforce such order in judicial proceedings and to impose civil money
penalties.  The Federal  Reserve,  the OCC and the other federal bank regulatory
agencies also proposed guidelines for asset quality and earnings standards.

A range of other provisions in FDICIA include requirements applicable to closure
of branches;  additional  disclosures  to  depositors  with respect to terms and
interest  rates  applicable  to  deposit  accounts;   uniform   regulations  for
extensions of credit secured by real estate;  restrictions  on activities of and
investments by state-chartered  banks;  modification of accounting  standards to
conform to generally accepted accounting  principles  including the reporting of
off-balance  sheet items and  supplemental  disclosure of estimated  fair market
value of assets and liabilities in financial  statements  filed with the banking
regulators;  increased penalties in making or failing to file assessment reports
with the FDIC;  greater  restrictions  on  extensions  of  credit to  directors,
officers and principal  shareholders;  and increased  reporting  requirements on
agricultural loans and loans to small businesses.

In August  1995,  the  Federal  Reserve,  OCC,  FDIC and other  federal  banking
agencies  published a final rule  modifying  their existing  risk-based  capital
standards to provide for  consideration of interest rate risk when assessing the
capital adequacy of a bank.  Under the final rule, the Federal Reserve,  the OCC
and the FDIC  must  explicitly  include a bank's  exposure  to  declines  in the
economic  value of its capital  due to changes in interest  rates as a factor in
evaluating a bank's capital adequacy. The Federal Reserve, the FDIC, the OCC and
other federal banking agencies also have adopted a joint agency policy statement
providing  guidance  to banks  for  managing  interest  rate  risk.  The  policy
statement  emphasizes the  importance of adequate  oversight by management and a
sound risk management  process.  The assessment of interest rate risk management
made by the banks'  examiners will be incorporated  into the banks' overall risk
management rating and used to determine the effectiveness of management.

Prompt  Corrective  Action.  FDICIA  requires  the federal  banking  regulators,
including the Federal Reserve,  the OCC and the FDIC, to take prompt  corrective
action with respect to depository  institutions  that fall below certain capital
standards  and  prohibits  any  depository  institution  from making any capital
distribution that would cause it to be  undercapitalized.  Institutions that are
not adequately  capitalized  may be subject to a variety of supervisory  actions
including, but not limited

                                     - 12 -

to, restrictions on growth,  investment  activities,  capital  distributions and
affiliate transactions and will be required to submit a capital restoration plan
which,  to be  accepted by the  regulators,  must be  guaranteed  in part by any
company  having  control  of the  institution  (such as the  Company).  In other
respects, FDICIA provides for enhanced supervisory authority,  including greater
authority for the appointment of a conservator or receiver for under-capitalized
institutions.  The  capital-based  prompt corrective action provisions of FDICIA
and   their   implementing   regulations   apply  to   FDIC-insured   depository
institutions.   However,  federal  banking  agencies  have  indicated  that,  in
regulating bank holding  companies,  the agencies may take appropriate action at
the holding  company  level based on their  assessment of the  effectiveness  of
supervisory  actions imposed upon  subsidiary  insured  depository  institutions
pursuant to the prompt corrective action provisions of FDICIA.

Insurance of Deposit  Accounts.  Under FDICIA,  as an FDIC-insured  institution,
each of the Banks is  required to pay deposit  insurance  premiums  based on the
risk it poses to the  insurance  fund.  The FDIC has authority to raise or lower
assessment  rates on insured  deposits  in order to achieve  certain  designated
reserve  ratios  in  the  insurance  funds  and  to  impose  special  additional
assessments.  Each  depository  institution  is assigned to one of three capital
groups:  "well capitalized,"  "adequately  capitalized" or "less than adequately
capitalized."  Within each capital  group,  institutions  are assigned to one of
three supervisory  subgroups:  "healthy,"  "supervisory concern" or "substantial
supervisory concern." Accordingly, there are nine combinations of capital groups
and supervisory subgroups to which varying assessment rates would be applicable.
An institution's assessment rate depends on the capital category and supervisory
category to which it is assigned.

Deposit  insurance  may  be  terminated  by the  FDIC  upon a  finding  that  an
institution  has  engaged  in unsafe or  unsound  practices,  is in an unsafe or
unsound  condition to continue  operations or has violated any  applicable  law,
regulation, rule, order or condition imposed by the FDIC. The management of each
of the Banks does not know any practice,  condition or violation that might lead
to termination of deposit insurance.

The Economic  Growth and Regulatory  Paperwork  Reduction Act of 1996 enacted on
September  30, 1996  provides  that  beginning  with  semi-annual  periods after
December 31, 1996, deposits insured by the Bank Insurance Fund ("BIF") will also
be assessed to pay interest on the bonds (the "FICO  Bonds")  issued in the late
1980s by the Financing Company to recapitalize the now defunct Federal Savings &
Loan Insurance  Company.  For purposes of the assessments to pay interest on the
FICO Bonds,  BIF deposits will be assessed at a rate of 20.0% of the  assessment
rate  applicable to SAIF deposits until December 31, 1999.  After the earlier of
December  31, 1999 or the date on which the last savings  association  ceases to
exist,  full pro rata sharing of FICO assessments will begin. The payment of the
assessment  to pay interest on the FICO Bonds should not  materially  affect the
Banks.

Federal  Reserve System.  The Banks are subject to Federal  Reserve  regulations
requiring  depository  institutions  to maintain  non-interest-earning  reserves
against  their  transaction   accounts   (primarily  NOW  and  regular  checking
accounts).  The Federal Reserve  regulations  generally require 3.0% reserves on
the first $46.5 million of transaction accounts plus 10.0% on the remainder. The
first $4.9 million of otherwise  reservable  balances (subject to adjustments by
the Federal Reserve) are exempted from the reserve  requirements.  The Banks are
in compliance with the foregoing requirements.

                                     - 13 -

Community  Reinvestment.   Under  the  Community  Reinvestment  Act  ("CRA"),  a
financial  institution has a continuing and affirmative  obligation,  consistent
with the safe and sound operation of such  institution,  to help meet the credit
needs of its entire community, including low- and moderate-income neighborhoods.
The CRA does  not  establish  specific  lending  requirements  or  programs  for
financial institutions nor does it limit an institution's  discretion to develop
the types of  products  and  services  that it  believes  are best suited to its
particular  community,  consistent  with the CRA. The CRA requires  each federal
banking agency,  in connection with its examination of a financial  institution,
to assess and assign one of four ratings to the institution's  record of meeting
the credit  needs of its  community  and to take such record into account in its
evaluation of certain  applications by the institution,  including  applications
for  charters,  branches and other  deposit  facilities,  relocations,  mergers,
consolidations,  acquisitions  of  assets or  assumptions  of  liabilities,  and
savings and loan holding  company  acquisitions.  The CRA also requires that all
institutions  make public  disclosure  of their CRA  ratings.  Each of the Banks
received  "satisfactory" ratings from either the Federal Reserve or OCC on their
most recent CRA performance evaluations.

In April 1995, the Federal  Reserve,  the OCC and other federal banking agencies
adopted  amendments  revising  their CRA  regulations.  Among other things,  the
amended  CRA  regulations  substitute  for the  prior  process-based  assessment
factors a new evaluation  system that rates an  institution  based on its actual
performance in meeting  community  needs.  In particular,  the focus is on three
tests: (i) a lending test, to evaluate the institution's  record of making loans
in its assessment  areas; (ii) an investment test, to evaluate the institution's
record of investing in community development  projects,  affordable housing, and
programs benefiting low or moderate income individuals and businesses; and (iii)
a service test, to evaluate the  institution's  delivery of services through its
branches,  ATMs and other offices.  The amended CRA regulations also clarify how
an institution's CRA performance would be considered in the application process.

Brokered Deposits.  Well-capitalized institutions are not subject to limitations
on brokered  deposits,  while an adequately  capitalized  institution is able to
accept, renew or rollover brokered deposits only with a waiver from the FDIC and
subject  to  certain   restrictions   on  the  yield  paid  on  such   deposits.
Undercapitalized  institutions  are not permitted to accept  brokered  deposits.
Each of the Banks is eligible to accept  brokered  deposits  (as a result of its
capital levels or having received a waiver) and may use this funding source from
time to time  when  management  deems  it  appropriate  from an  asset/liability
management perspective.

Enforcement  Actions.   Federal  and  state  statutes  and  regulations  provide
financial  institution  regulatory  agencies with great flexibility to undertake
enforcement  action against an institution  that fails to comply with regulatory
requirements,  particularly capital  requirements.  Possible enforcement actions
range  from  the  imposition  of  a  capital  plan  and  capital   directive  to
receivership, conservatorship or the termination of deposit insurance.

                                     - 14 -

Interstate  Banking and  Branching  Legislation.  On  September  29,  1994,  the
Riegle-Neal  Interstate  Banking  and  Efficiency  Act of 1994 (the  "Interstate
Banking  Act")  was  enacted.  Under  the  Interstate  Banking  Act,  adequately
capitalized  and  adequately  managed bank holding  companies will be allowed to
acquire  banks across state lines subject to certain  limitations.  In addition,
under the Interstate Banking Act, effective June 1, 1997, banks are permitted to
merge with one another  across  state lines and thereby  create a main bank with
branches in separate states.  After establishing  branches in a state through an
interstate  merger  transaction,  a bank can  establish  and acquire  additional
branches at any location in the state where any bank involved in the  interstate
merger could have established or acquired branches under applicable  federal and
state law.

Recent Legislation. On November 12, 1999, the Gramm-Leach-Bliley Act ("GLB Act")
was  enacted.  The  GLB  Act  amended  or  repealed  certain  provisions  of the
Glass-Steagall Act and other legislation and, among other things,  establishes a
comprehensive   framework  to  permit   affiliations   among  commercial  banks,
securities  firms and  insurance  companies.  In addition,  the GLB Act contains
provisions intended to safeguard consumer financial  information in the hands of
financial  service  providers  primarily by requiring  such entities to disclose
their privacy policies to their customers and allowing customers to "opt out" of
having their financial services providers disclose their confidential  financial
information  to third  parties,  subject  to  certain  exceptions.  The  federal
regulatory  agencies have not as of this date issued final regulations under the
GLB Act. The Company  does not believe the GLB Act will have a material  adverse
affect upon its operations in the near term.  However, to the extent the GLB Act
permits  banks,  securities  firms and  insurance  companies to  affiliate,  the
financial  services industry may experience  further  consolidation.  This could
result in a growing number of larger financial  institutions  that offer a wider
variety of financial  services  than the Company  currently  offers and that can
aggressively compete in the markets the Company currently serves.

MONETARY POLICY AND ECONOMIC CONDITIONS

The  earnings  of banks and bank  holding  companies  are  affected  by  general
economic  conditions  and also by the fiscal and  monetary  policies  of federal
regulatory  agencies,   including  the  Federal  Reserve.  Through  open  market
transactions,  variations in the discount rate and the  establishment of reserve
requirements,  the Federal Reserve exerts  considerable  influence over the cost
and availability of funds obtainable for lending or investing.

The above monetary and fiscal  policies and resulting  changes in interest rates
have affected the operating  results of all commercial banks in the past and are
expected  to do so in  the  future.  The  Banks  and  their  respective  holding
companies  cannot  fully  predict the nature or the extent of any effects  which
fiscal or monetary policies may have on their business and earnings.

SUPPLEMENTAL STATISTICAL DATA

Pages 3, 45 and 46 of the 1999 Annual Report to Shareholders  and Item 8 of this
Form 10-K contain supplemental  statistical data as required by The Exchange Act
Industry Guide 3 which is incorporated into Regulation S-K of the Securities and
Exchange  Acts.  This data  should  be read in  conjunction  with the  Company's
Consolidated Financial Statements and notes thereto, and Management's Discussion
and Analysis which are contained in its 1999 Annual Report to Shareholders filed
herewith as Exhibit 13.1 and incorporated herein by reference.

                                     - 15 -

ITEM 2. PROPERTIES

The  Company's  executive  offices are located in the main bank facility of Lake
Forest Bank. Lake Forest Bank has six physical  banking  locations.  Lake Forest
Bank's main bank facility is located at 727 N. Bank Lane, Lake Forest, Illinois,
and is a three story,  37,000 square foot brick  building that includes a 15,200
square foot  addition that was  completed in May 1999.  The Company's  executive
offices and staff of the holding company,  Lake Forest Bank and WAMC are located
on the second and third  floors of the  addition  with first floor  retail space
leased to unrelated  third  parties.  Lake Forest Bank  constructed  a drive-in,
walk-up  banking  facility  on land  leased  from the City of Lake Forest on the
corner of Bank Lane and Wisconsin Avenue in Lake Forest, approximately one block
north of the main banking facility.  Lake Forest Bank also leases a 1,200 square
foot, a full service banking facility at 103 East Scranton Avenue in Lake Bluff,
Illinois;  a 2,100 square foot, a full service banking facility on the west side
of Lake Forest,  Illinois at 810 South Waukegan Road, and a drive-in and walk-up
banking facility at 911 S. Telegraph Road in the West Lake Forest Train Station.
Lake  Forest  Bank  also  maintains  a small  office  facility  at a  retirement
community known as Lake Forest Place at 1100 Pembridge Drive in Lake Forest.  In
early 2000, a temporary branch facility was opened in the Highwood-Fort Sheridan
area with final  construction of a permanent  building  expected to be completed
later in 2000.  Lake Forest Bank maintains ATMs at each of its locations  except
the 810 South Waukegan Road facility. Lake Forest Bank has no offsite ATMs.

Hinsdale Bank currently has four physical  banking  locations,  all of which are
owned.  The main bank facility is a two story brick building  located at 25 East
First Street in downtown  Hinsdale,  Illinois.  The 1,000 square foot  drive-in,
walk-up banking facility at 130 West Chestnut is  approximately  two blocks west
of the main banking  facility.  Hinsdale Bank also has full service  branches in
Clarendon  Hills and Western  Springs.  The  buildings  in  Clarendon  Hills and
Western  Springs are partially used for bank purposes,  with the remainder being
leased to unrelated  parties.  Hinsdale  Bank  maintains one ATM machine at each
location,  with the exception of Clarendon Hills,  which has two.  Hinsdale Bank
has no offsite ATMs.

North Shore Bank currently has seven  physical  banking  locations.  North Shore
Bank owns the main bank facility,  a one story brick building that is located at
1145 Wilmette Avenue in downtown Wilmette,  Illinois. North Shore Bank also owns
a 9,600  square foot  drive-in,  walk-up  banking  facility at 720 12th  Street,
approximately one block west of the main banking facility. North Shore Bank also
leases a full service banking  facility at 362 Park Avenue in Glencoe,  Illinois
and  a  branch   banking   facility  in  Winnetka,   Illinois  where  it  leases
approximately 4,000 square feet. In 1998, North Shore Bank opened a drive-up and
ATM for the  Glencoe  branch  and a small  facility  at 4th Street and Linden in
Wilmette.  In 1999,  a full  service  leased  facility  was  opened  in  Skokie,
Illinois.  North  Shore Bank  maintains  ATMs at each of its  locations,  except
Winnetka, and has no offsite ATMs.

                                     - 16 -

Libertyville Bank currently has three physical banking  locations.  Libertyville
Bank owns the main bank facility,  which is a 13,000 square foot two story brick
building  located  at 507  North  Milwaukee  Avenue  in  downtown  Libertyville,
Illinois.  Libertyville  Bank also owns a 2,500  square foot  drive-in,  walk-up
banking facility at 201 Hurlburt Court,  approximately  five blocks southeast of
the main  banking  facility.  A leased  branch  facility  located  at 1167 South
Milwaukee Avenue in south Libertyville was opened in October 1998.  Libertyville
Bank  maintains  ATMs  at  each  of its  banking  locations  and at one  offsite
location.

Barrington Bank currently has one physical  banking  location at 201 South Hough
Street in  Barrington,  Illinois  which is a 12,700 square foot, two story frame
construction building that has an attached  drive-through  facility.  Barrington
Bank has two ATMs, but no offsite ATMs.

In September 1998, Crystal Lake Bank moved into its permanent two story,  12,000
square foot main bank facility located at 70 Williams Street in downtown Crystal
Lake, Illinois. In March 1999, Crystal Lake Bank opened a drive-up facility that
is located in the downtown area, near the main bank facility. In September 1999,
Crystal Lake Bank opened a full service owned  facility  located at 1000 McHenry
Avenue  in south  Crystal  Lake.  Crystal  Lake  Bank  maintains  an ATM at each
location.

FIFC's  offices  are  located  at 520 Lake  Cook  Road,  Suite  300,  Deerfield,
Illinois.  FIFC leases  approximately 12,000 square feet of office space under a
contract  that expires in the year 2000.  In mid-2000,  FIFC will  relocate to a
facility in Northbrook that was purchased in late 1999.

WAMC's executive and operations staff are based in office space leased from Lake
Forest Bank. WAMC also leases office space for its trust  professionals  at Lake
Forest Bank, Hinsdale Bank, North Shore Bank and Barrington Bank.

Tricom  leases  approximately  10,700  square feet of office space in Milwaukee,
Wisconsin at 11270 West Park Place, Suite 100.

See Note 6 to the Consolidated Financial Statements contained in the 1999 Annual
Report to Shareholders filed herewith as Exhibit 13.1 and incorporated herein by
reference.

                                     - 17 -

ITEM 3. LEGAL PROCEEDINGS

The Company and its subsidiaries,  from time to time, are subject to pending and
threatened  legal  action  and  proceedings  arising in the  ordinary  course of
business.  Any such litigation  currently pending is incidental to the Company's
business and, based on information currently available to management, management
believes  the outcome of such  actions or  proceedings  will not have a material
adverse effect on the operations or financial position of the Company.


ITEM 4. SUBMISSION OF MATTERS TO A VOTE OF SECURITY HOLDERS

No  matters  were  submitted  to a vote of  security  holders  during the fourth
quarter of 1999.



                                    PART II.

ITEM 5. MARKET FOR REGISTRANT'S COMMON EQUITY AND RELATED STOCKHOLDER MATTERS

The  Company's  common stock is traded on The Nasdaq Stock  Market(R)  under the
symbol  WTFC.  The  following  table  sets  forth the high and low sales  prices
reported on Nasdaq for the Common Stock during 1999 and 1998.



                                                    1999                               1998
                                                    ----                               ----
                                             HIGH            LOW               HIGH              LOW
                                             ----            ---               ----              ---
                                                                                   
Fourth quarter                             $ 18.19          14.69              20.13           16.50
Third quarter                                19.12          16.19              23.00           17.13
Second quarter                               26.75          17.50              20.38           17.38
First quarter                                20.25          15.50              18.50           16.50


APPROXIMATE NUMBER OF EQUITY SECURITY HOLDERS
- ---------------------------------------------

As of February 29, 2000 there were 1,473 shareholders of record of the Company's
common stock.

                                     - 18 -

DIVIDENDS ON COMMON STOCK
- -------------------------

In January 2000, the Company's Board of Directors approved the first semi-annual
cash dividend on its common stock. The dividend in the amount of $0.05 per share
was paid on February 24, 2000 to shareholders of record as of February 10, 2000.
The  declaration  of dividends is at the  discretion of the  Company's  Board of
Directors  and  depends  upon   earnings,   capital   requirements,   regulatory
limitations,  tax  considerations,  the operating and financial condition of the
Company  and other  factors.  Additionally,  the  payment  of  dividends  may be
restricted  under  certain  terms of the Company's  Trust  Preferred  Securities
offering.

Because the Company's  consolidated net income consists largely of net income of
the Banks, FIFC and Tricom,  the Company's ability to pay dividends depends upon
its  receipt  of  dividends  from  these  entities.  The  Banks'  ability to pay
dividends  is  regulated  by  banking  statutes.   See  "Financial   Institution
Regulation  Generally  -  Dividend  Limitations"  on page 10 of this Form  10-K.
During  1998,  Lake Forest Bank paid $8.25  million of dividends to the Company.
There were no dividends  paid by the Banks to the Company  during either 1999 or
1997.  In  addition,  Crystal  Lake Bank is subject to  additional  restrictions
prohibiting  the payment of dividends by a de novo bank in its first three years
of  operations.  The de novo period will end in December  2000 for Crystal  Lake
Bank.  In addition,  the payment of dividends  may be  restricted  under certain
financial covenants in the Company's revolving line of credit.

Reference is made to Note 14 to the Consolidated  Financial Statements contained
in the 1999 Annual  Report to  Shareholders,  attached  hereto as Exhibit  13.1,
which is incorporated herein by reference, for a description of the restrictions
on the ability of certain  subsidiaries  to transfer funds to the Company in the
form of dividends.

RECENT SALES OF UNREGISTERED SECURITIES
- ---------------------------------------

In  Hinsdale  Bank's  acquisition  of 100% of the  stock  of  Tricom,  completed
effective as of October 1, 1999,  the Company  issued  227,635  shares of Common
Stock as part of the purchase price to the two individual selling  shareholders.
Such  shares  were  issued and sold  without  registration  in  reliance  on the
exemption provided by Section 4(2) of the Securities Act of 1933.

On November  17, 1999,  the Company  sold 352,942  shares of Common Stock for $6
million in cash directly to two  institutional  investors in a private placement
transaction exempt from registration pursuant to Section 4(2).

ITEM 6. SELECTED FINANCIAL DATA

Certain  information  required in response to this item is contained in the 1999
Annual Report to Shareholders under the caption "Selected Financial  Highlights"
and is  incorporated  herein by  reference.  The Company  had no cash  dividends
declared  during  any period  during the last five  years.  The  Company  had no
Preferred  Stock   outstanding  at  December  31,  1999,  1998,  1997  or  1996.
Predecessors of the Company did have $503,000 of Preferred Stock  outstanding at
December 31, 1995.

                                     - 19 -

ITEM 7. MANAGEMENT'S  DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS
OF OPERATIONS

The  information  required  in response  to this item is  contained  in the 1999
Annual Report to  Shareholders  under the caption  "Management's  Discussion and
Analysis of Financial Condition and Results of Operations".  This discussion and
analysis of  financial  condition  and results of  operations  should be read in
conjunction  with  the  Consolidated  Financial  Statements  and  notes  thereto
contained in the 1999 Annual Report to Shareholders.

ITEM 7A. QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISKS

Certain  information  required in response to this item is contained in the 1999
Annual Report to  Shareholders  under the caption  "Management's  Discussion and
Analysis of Financial  Condition  and Results of  Operations  -  Asset-Liability
Management"  and in Notes 15 and 16 to the  Consolidated  Financial  Statements,
which are incorporated  herein by reference.  This information should be read in
conjunction  with the  complete  Consolidated  Financial  Statements  and  notes
thereto contained in the 1999 Annual Report to Shareholders.

ITEM 8.  FINANCIAL STATEMENTS AND SUPPLEMENTARY DATA

The  information  required  in response  to this item is  contained  in the 1999
Annual  Report  to  Shareholders  under  the  caption  "Consolidated   Financial
Statements," and is incorporated herein by reference.  Also, refer to Item 14 of
this Report for the Index to Financial Statements.

SUPPLEMENTAL STATISTICAL DATA
- -----------------------------

                              SECURITIES PORTFOLIO

Tables presenting the carrying amounts and gross unrealized gains and losses for
securities held-to-maturity and available-for-sale at December 31, 1999 and 1998
are  included by reference to Note 2 to the  Consolidated  Financial  Statements
included in the 1999 Annual Report to Shareholders, which is incorporated herein
by  reference.  Maturities  of  securities  as of December  31, 1999 by maturity
distribution are as follows (in thousands):




                                                                                       Mortgage-     Federal
                                      Within      From 1       From 5 to     After      backed       Agency
                                      1 Year   to 5 years      10 years    10 years    securities   Bank stock      Total
                                     --------  ----------      --------    --------    ----------   ----------    --------
                                                                                              
U.S. Treasury obligations             $ 1,242      37,929           -           -            -             -       39,171
Federal agency obligations             40,711      24,597       4,876           -            -             -       70,184
Municipal securities                      498       1,545           -       1,995            -             -        4,038
Corporate notes and other              23,390       4,015       1,028      10,592            -             -       39,025
Mortgage-backed securities (1)              -           -           -           -       46,124             -       46,124
Federal Agency Bank stock (2)               -           -           -           -            -         7,253        7,253
                                     --------  ----------      --------    --------    ----------   ----------    --------

      Total                          $ 65,841      68,086       5,904      12,587       46,124         7,253      205,795
                                     ========  ==========      ========    ========    ==========   ==========    ========


                                     - 20 -

The weighted average yield for each range of maturities of securities,  on a tax
equivalent basis, is shown below as of December 31, 1999:




                                                                                       Mortgage-     Federal
                                      Within      From 1       From 5 to     After      backed       Agency
                                      1 Year   to 5 years      10 years    10 years    securities   Bank stock      Total
                                     --------  ----------      --------    --------    ----------   ----------    --------
                                                                                              
U.S. Treasury obligations               5.13%       5.28%           -           -            -             -        5.28%
Federal agency obligations              5.45%       6.06%       5.59%           -            -             -        5.67%
Municipal securities                    5.80%       6.54%           -       8.25%            -             -        7.29%
Corporate notes and other               5.16%       7.03%       6.61%       7.21%            -             -        5.98%
Mortgage-backed securities (1)              -           -           -           -        7.38%             -        7.38%
Federal Agency Bank stock (2)               -           -           -           -            -         6.85%        6.85%
                                     --------  ----------      --------    --------    ----------   ----------    --------

      Total                             5.34%       5.69%       5.77%       7.37%        7.38%         6.85%        6.11%
                                     ========  ==========      ========    ========    ==========   ==========    ========
<FN>
(1)  Mortgage-backed  security maturities may differ from contractual maturities
     because  the  underlying  mortgages  may be called or prepaid  without  any
     penalties. Therefore, these securities are not included within the maturity
     categories above.
(2)  Includes  stock of the Federal  Reserve  Bank and of the Federal  Home Loan
     Bank.
</FN>



                                 LOAN PORTFOLIO

The following  table shows the Company's loan portfolio by category for the five
previous fiscal years (in thousands):



At December 31                                      1999              1998            1997           1996            1995
- -----------                                         ----              ----            ----           ----            ----


                                                                                                       
Commercial/commercial real estate                    $ 485,776         366,229        235,483         182,403         101,271
Home equity                                            139,194         111,537        116,147          87,303          54,592
Residential real estate                                111,026          91,525         61,611          51,673          37,074
Premium finance receivables                            225,239         183,165        131,952          59,240          15,703
Indirect auto                                          255,434         210,137        139,296          91,211          37,323
Tricom finance receivables                              17,577               -              -               -               -
Installment and other                                   49,925          34,650         32,153          23,717          14,032
                                               ----------------    ------------    -----------    ------------    ------------
   Total loans                                       1,284,171         997,243        716,642         495,547         259,995
Less: Unearned income                                    5,922           5,181          4,011           2,999           1,764
                                               ----------------    ------------    -----------    ------------    ------------
   Total loans, net of
      unearned income                                $1,278,249        992,062        712,631         492,548         258,231
                                               ================    ============    ===========    ============    ============


Commercial and commercial  real estate loans.  The commercial  loan component is
comprised primarily of commercial real estate loans, lines of credit for working
capital purposes, and term loans for the acquisition of equipment. This category
also includes certain  commercial  equipment  leases.  Commercial real estate is
predominantly owner occupied and secured by a first mortgage lien and assignment
of rents on the  property.  Equipment  loans  and  leases  are  generally  fully
amortized  over 24 to 60 months and  secured by titles  and/or  U.C.C.  filings.
Working capital lines are generally renewable annually and supported by business
assets, personal guarantees and,

                                     - 21 -

oftentimes,  additional  collateral.  Commercial  business  lending is generally
considered  to involve a higher  degree of risk than  traditional  consumer bank
lending.  The vast  majority  of  commercial  loans are made  within  the Banks'
immediate  market areas. The increase in this loan category can be attributed to
additional  banking  facilities,  an emphasis on  business  development  calling
programs and superior servicing of existing  commercial loan customers which has
increased referrals.

In  addition  to the  home  mortgages  originated  by  the  Banks,  the  Company
participates  in mortgage  warehouse  lending by  providing  interim  funding to
unaffiliated  mortgage brokers to finance  residential  mortgages  originated by
such brokers for sale into the  secondary  market.  The  Company's  loans to the
mortgage brokers are secured by the business assets of the mortgage companies as
well as the  underlying  mortgages,  the  majority  of which  are  funded by the
Company on a loan-by-loan  basis after they have been  pre-approved for purchase
by third  party end lenders who  forward  payment  directly to the Company  upon
their acceptance of final loan documentation.  In addition, the Company may also
provide  interim  financing  for  packages of mortgage  loans on a bulk basis in
circumstances where the mortgage brokers desire to competitively bid a number of
mortgages for sale as a package in the secondary market.  Typically, the Company
will serve as sole funding source for its mortgage  warehouse  lending customers
under short-term  revolving credit agreements.  Amounts advanced with respect to
any particular  mortgages are usually  required to be repaid within 15 days. The
Company has developed strong relationships with a number of mortgage brokers and
is seeking to expand its customer base for this specialty business.

The  following  table  classifies  the  commercial  loan  portfolio  category at
December 31, 1999 by date at which the loans mature:



                                                                           FROM ONE
                                                        ONE YEAR            TO FIVE         AFTER
                                                         OR LESS             YEARS        FIVE YEARS         TOTAL
                                                       ------------     ------------     ------------     ------------
                                                                          (IN THOUSANDS)
                                                                                                
           Commercial loans and commercial real
             estate loans...........................    $ 208,062          225,074           52,640         485,776
           Premium finance receivables, net of
             unearned income........................      219,341                -                -         219,341
           Tricom finance receivables...............       17,577                -                -          17,577


Of those loans maturing after one year,  approximately $228.5 million have fixed
rates.

Home  equity  loans.  The  Company's  home equity loan  products  are  generally
structured as lines of credit secured by first or second position mortgage liens
on  the  underlying  property  with  loan-to-value  ratios  not  exceeding  80%,
including prior liens, if any. The Banks' home equity loans feature  competitive
rate structures and fee arrangements.  In addition, the Banks periodically offer
promotional home equity loan products as part of their marketing  strategy often
featuring lower introductory rates.

                                     - 22 -

Indirect auto loans. As part of its strategy to pursue specialized earning asset
niches to augment loan generation within the Banks' target markets,  the Company
finances fixed rate  automobile  loans funded  indirectly  through  unaffiliated
automobile  dealers.  As of December 31,  1999,  indirect  auto loans  comprised
approximately 84% of the Company's consumer loan portfolio.  Indirect automobile
loans are  secured  by new and used  automobiles  and are  generated  by a large
network of automobile dealers located in the Chicago area with which the Company
has established  relationships.  These credits generally have an average initial
balance of  approximately  $15,000  and have an  original  maturity  of 36 to 60
months with the average actual maturity,  as a result of prepayments,  estimated
to be approximately  35-40 months. The Company does not currently  originate any
significant  level  of  sub-prime  loans,  which  are made to  individuals  with
impaired credit  histories at generally  higher interest rates, and accordingly,
with higher levels of credit risk.  The risk  associated  with this portfolio is
diversified among many individual borrowers. Management continually monitors the
dealer  relationships  and the Banks are not  dependent  on any one  dealer as a
source of such loans.  Like other  consumer  loans,  the indirect auto loans are
subject to the Banks' stringent credit standards.

Residential  real  estate  mortgages.   The  residential  real  estate  category
predominantly  includes  one-to-four  family adjustable rate mortgages that have
repricing  terms  generally  from  one to  three  years,  construction  loans to
individuals,  bridge financing loans for qualifying customers and mortgage loans
held for sale into the secondary market. The adjustable rate mortgages are often
non-agency conforming,  may have terms based on differing indexes, and relate to
properties  located  principally  in the Chicago  metropolitan  area or vacation
homes owned by local residents.  Adjustable-rate mortgage loans decrease, but do
not eliminate,  the risks  associated  with changes in interest  rates.  Because
periodic and lifetime  caps limit the interest  rate  adjustments,  the value of
adjustable-rate  mortgage  loans  fluctuates  inversely with changes in interest
rates.  In addition,  as interest rates increase,  the required  payments by the
borrower increases,  thus increasing the potential for default. The Company does
not generally  originate  loans for its own portfolio with long-term fixed rates
due to interest  rate risk  considerations,  however,  the Banks do  accommodate
customer  requests for fixed rate loans by  originating  and selling these loans
into the secondary  market,  in connection  with which the Company  receives fee
income, or by selectively including certain of these loans within the Banks' own
portfolios.  A portion of the loans sold by the Banks into the secondary  market
is to the Federal National Mortgage  Association  ("FNMA") whereby the servicing
of those loans is retained. The amount of loans serviced for FNMA as of December
31, 1999 and 1998 was $87.1 million and $82.1 million,  respectively.  All other
mortgage  loans held for sale are sold into the  secondary  market  without  the
retention of servicing rights.

Premium finance receivables.  The Company originates premium finance receivables
through FIFC,  which,  in turn, are mostly sold to the Banks and retained within
their loan  portfolios.  In 1999, the Company began selling a portion of premium
finance receivable  originations to an unrelated  financial  institution,  which
resulted in the recognition of gains from the sales of these  receivables.  FIFC
sold  approximately  $69 million of  receivables to this third party in 1999 and
recognized  approximately  $1.0 million in gains.  As of December 31, 1999,  the
balance  of  these   receivables   that  are  being  serviced  by  FIFC  totaled
approximately $46.2 million.  All premium finance receivables are subject to the
Company's stringent credit standards,  and substantially all such loans are made
to  commercial  customers.   The  Company  rarely  finances  consumer  insurance
premiums.

                                     - 23 -

FIFC generally  offers financing of  approximately  80% of an insurance  premium
primarily to  commercial  purchasers  of property  and  casualty  and  liability
insurance who desire to pay insurance  premiums on an  installment  basis.  FIFC
markets  its  financial  services  primarily  by  establishing  and  maintaining
relationships with medium and large insurance agents and brokers and by offering
a  high  degree  of  service  and  innovative  products.  Senior  management  is
significantly  involved in FIFC's marketing  efforts,  currently  focused almost
exclusively  on commercial  accounts.  Loans are  originated by FIFC's own sales
force by working with insurance agents and brokers throughout the United States.
As of December 31, 1999, FIFC had the necessary  licensing and other  regulatory
approvals to do business in all 50 states and the District of Columbia.

In financing  insurance  premiums,  the Company does not assume the risk of loss
normally borne by insurance carriers.  Typically,  the insured buys an insurance
policy  from an  independent  insurance  agent or broker  who  offers  financing
through FIFC. The insured typically makes a down payment of approximately 15% to
25% of the total premium and signs a premium  finance  agreement for the balance
due, which amount FIFC disburses directly to the insurance carrier or its agents
to satisfy the unpaid premium  amount.  The average  initial  balance of premium
finance loans is approximately $13,000 and the average term of the agreements is
approximately 10 months.  As the insurer earns the premium ratably over the life
of the  policy,  the  unearned  portion of the  premium  secures  payment of the
balance due to FIFC by the insured.  Under the terms of the  Company's  standard
form of financing  contract,  the Company has the power to cancel the  insurance
policy if there is a default  in the  payment  on the  finance  contract  and to
collect the unearned portion of the premium from the insurance  carrier.  In the
event of cancellation of a policy,  the cash returned in payment of the unearned
premium  by the  insurer  should be  sufficient  to cover the loan  balance  and
generally the interest and other charges due as well.  The major risks  inherent
in this type of  lending  are (1) the risk of fraud on the part of an  insurance
agent  whereby the agent  fraudulently  fails to forward  funds to the insurance
carrier or to FIFC, as the case may be; (2) the risk that the insurance  carrier
becomes  insolvent and is unable to return unearned premiums related to loans in
default;  (3) for policies that are subject to an audit by the insurance carrier
(i.e.  workers  compensation  policies where the insurance carrier can audit the
insured actual payroll records),  the risk that the initial  underwriting of the
policy was such that the premium paid by the insured are not sufficient to cover
the a entire return  premium in the event of default;  and (4) that the borrower
is unable to  ultimately  satisfy  the debt in the event the  returned  unearned
premium is insufficient  to retire the loan.  FIFC has established  underwriting
procedures to reduce the potential of loss  associated  with the  aforementioned
risks and has  systems in place to  continually  monitor  conditions  that would
indicate  an  increase  in  risk  factors  and to act on  situations  where  the
Company's collateral position is in jeopardy.

Tricom finance  receivables.  The October 1999  acquisition of Tricom added this
category,   which  consists  of  high-yielding  short-term  accounts  receivable
financing to clients in the temporary  staffing industry located  throughout the
United  States.  The clients'  working  capital needs arise  primarily  from the
timing differences  between weekly payroll funding and monthly  collections from
customers.  The  primary  security  for  Tricom's  finance  receivables  are the
accounts  receivable of its clients and personal  guarantees.  Tricom  generally
advances  80-95%  based on various  factors  including  the  client's  financial
condition,  the length of client  relationship  and the  nature of the  client's
customer  business  lines.  Typically,  Tricom  will  also  provide  value-added
out-sourced  administrative  services  to many of  these  clients,  such as data
processing of payrolls,  billing and cash management  services,  which generates
additional fee income.

                                     - 24 -

Installment and Other.  Included in the installment and other loan category is a
wide variety of personal and consumer loans to individuals.  The Banks have been
originating  consumer loans in recent years in order to provide a wider range of
financial  services to their  customers.  Consumer loans  generally have shorter
terms and higher  interest rates than mortgage loans but generally  involve more
credit risk than mortgage loans due to the type and nature of the collateral.

The Company had no loans to businesses or  governments  of foreign  countries at
any time during the reporting periods.


                       RISK ELEMENTS IN THE LOAN PORTFOLIO

For analysis and review of the allowance for possible loan losses;  non-accrual,
past due and  restructured  loans;  other real estate owned;  potential  problem
loans; and loan concentrations,  reference is made to the "Credit Risk and Asset
Quality"  section of the  Management's  Discussion  and  Analysis  of  Financial
Condition and Results of  Operations  of the 1999 Annual Report to  Shareholders
filed herewith as Exhibit 13.1, and incorporated herein by reference.

An  allocation  of the  allowance for possible loan losses by major loan type is
presented below (dollars in thousands):



                                          December 31, 1999               December 31, 1998              December 31, 1997
                                    ------------------------------- ----------------------------- ---------------------------------
                                                     % of loans                      % of loans                     % of loans
                                                       in each                         in each                        in each
                                                     category to                     category to                   category to
                                        Amount       total loans        Amount       total loans      Amount        total loans
                                    ------------     ------------    ------------   ------------    ------------   ------------
                                                                                                     
  Commercial and
    commercial real estate..........    $ 3,435          38%            $ 2,480          37%           $1,490          33%
  Home equity.......................      1,146          11               1,046          11               580          16
  Residential real estate...........        126           9                  81           9                43           9
  Premium finance...................        721          17                 919          18               702          18
  Indirect auto.....................      1,947          20               1,205          21               679          19
  Tricom finance receivables.               120           1                   -           -                 -           -
  Installment and other.............        469           4                 494           4               218           5
  Unallocated.......................        819           -                 809           -             1,404           -
                                    ------------     ------------    ------------   ------------    ------------   ------------

 Total..............................    $ 8,783         100%            $ 7,034         100%           $5,116          100%
                                    ============     ============    ============   ============    ============   ============


The above allocation is made for analytical purposes. It is not anticipated that
charge-offs  during the year  ending  December  31,  2000 will exceed the amount
allocated to any  individual  category of loan.  For further  review of the loan
loss  provision and the allowance for possible loan losses  reference is made to
the "Credit Risk and Asset Quality" section of the  Management's  Discussion and
Analysis of Financial  Condition  and Results of  Operations  of the 1999 Annual
Report to Shareholders  filed herewith as Exhibit 13.1, and incorporated  herein
by reference.

                                     - 25 -

                                    DEPOSITS

The  following  table sets forth the  scheduled  maturities  of time deposits in
denominations of $100,000 or more at December 31, 1999 (in thousands):

  Maturing within 3 months ...............................        $ 113,393
  After 3 but within 6 months ............................           84,991
  After 6 but within 12 months ...........................          161,706
  After 12 months ........................................           72,892
                                                              ---------------

    Total ................................................        $ 432,982
                                                              ===============


                           Return on Equity and Assets

 The following table presents  certain ratios  relating to the Company's  equity
and assets:



Year Ended December 31                                                1999            1998           1997
- ----------------------                                                ----            ----           ----

                                                                                             
Return on average total assets .................................       0.63%           0.53%          0.56%
Return on average common shareholders' equity ..................      11.58%           8.68%          7.88%
Dividend payout ratio ..........................................       0.00%           0.00%          0.00%

Average equity to average total assets .........................        5.4%            6.1%           7.2%
Ending total risk based capital ratio ..........................        8.4%            9.7%           9.4%
Leverage ratio .................................................        7.1%            7.5%           6.6%



                              SHORT-TERM BORROWINGS

The information  required in connection with Short-Term  Borrowings is contained
in the  "Analysis  of  Financial  Condition -  Short-Term  Borrowings  and Notes
Payable"  sections of the  Management's  Discussion  and  Analysis of  Financial
Condition and Results of  Operations  in the 1999 Annual Report to  Shareholders
filed herewith as Exhibit 13.1, and is incorporated herein by reference.  During
1999,  the  Company  entered  into  sales  of  securities  under  agreements  to
repurchase  ("reverse repurchase  agreements").  Fixed-coupon reverse repurchase
agreements  are  treated  a  financings,   and  the  obligations  to  repurchase
securities  sold are  reflected as short-term  borrowings in the Company's  1999
Annual  Report to  Shareholders  under the caption  "Consolidated  Statements of
Condition". The dollar amounts of securities underlying the agreements remain in
the  available-for-sale  securities  section of the  Consolidated  Statements of
Condition.  During 1999,  the maximum  month-end  balance of reverse  repurchase
agreements  was $82.4  million.  At December  31,  1999,  securities  sold under
agreements to repurchase  consisted of U.S.  government  agency  mortgage-backed
securities.  These  securities  underlying the agreements  were delivered to the
dealer who  arranged the  transactions.  The  agreements  require the Company to
repurchase the same securities.

                                     - 26 -

ITEM  9.  CHANGES  IN AND  DISAGREEMENTS  WITH  ACCOUNTANTS  ON  ACCOUNTING  AND
FINANCIAL DISCLOSURE

At its regular board meeting on April 29, 1999, the Company's Board of Directors
voted to approve the Audit  Committee's  recommendation to engage the accounting
firm of Ernst & Young LLP as independent accountants for the year ended December
31, 1999. The work of KPMG LLP was  terminated on April 29, 1999,  subsequent to
the Form 10-K report for December 31, 1998,  which was filed with the Securities
and Exchange  Commission on March 30, 1999.  During the audits of the two fiscal
years ended  December 31, 1998 and the  subsequent  interim period through April
29, 1999, there were no disagreements  with KPMG LLP on any matter of accounting
principles or practices,  financial statement  disclosure,  or auditing scope or
procedures, which disagreements if not resolved to their satisfaction would have
caused them to make  reference in  connection  with their opinion to the subject
matter of the  disagreement,  nor have there  been any  reportable  events.  The
information required in response to this item is contained in the April 29, 1999
Form 8-K that was filed with the Commission on May 6, 1999, and is  incorporated
herein by reference.


                                    PART III

ITEM 10. DIRECTORS AND EXECUTIVE OFFICERS OF THE REGISTRANT

The  information  required  in response  to this item will be  contained  in the
Company's  definitive  Proxy  Statement (the "Proxy  Statement")  for its Annual
Meeting of Shareholders  to be held May 25, 2000 under the caption  "Management"
and is incorporated herein by reference.


ITEM 11. EXECUTIVE COMPENSATION

The  information  required  in response  to this item will be  contained  in the
Company's  Proxy  Statement under the caption  "Executive  Compensation"  and is
incorporated herein by reference.


ITEM 12. SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT

Information with respect to security  ownership of certain beneficial owners and
management is incorporated by reference to the section "Principal  Shareholders"
in the Proxy  Statement for the Annual Meeting of Shareholders to be held on May
25, 2000.

ITEM 13. CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS

The information required in response to this item will be contained in the Proxy
Statement under the caption "Certain  Transactions," and is incorporated  herein
by reference.

                                     - 27 -

                                     PART IV

ITEM 14. EXHIBITS, FINANCIAL STATEMENT SCHEDULES, AND REPORTS ON
                          FORM 8-K

(a)      Documents filed as part of this Report:

         1., 2.      Financial Statements and Schedules
                     ----------------------------------

        The following  financial  statements of Wintrust Financial  Corporation,
        incorporated   herein  by  reference  to  the  1999  Annual   Report  to
        Shareholders  filed as Exhibit 13.1,  are filed as part of this document
        pursuant to Item 8. Financial Statements and Supplementary Data:

        - Consolidated Statements of Condition as of December 31, 1999 and 1998
        - Consolidated  Statements  of Income for the  Years Ended  December 31,
          1999, 1998 and 1997
        - Consolidated  Statements of  Changes in  Shareholders'  Equity for the
          Years Ended December 31, 1999, 1998 and 1997
        - Consolidated Statements of Cash Flows for the Years Ended December 31,
          1999, 1998 and 1997
        - Notes to Consolidated Financial Statements
        - Independent Auditors' Reports

         No schedules are required to be filed with this report.

3.      Exhibits  (Exhibits  marked with a "*" denote  management  contracts  or
        --------    compensatory plans or arrangements)

2.1     Stock Purchase Agreement Among Wintrust  Financial  Corporation and John
        Leopold  and Mark Kahn  dated  September  16,  1999 in  relation  to the
        acquisition of Tricom,  Inc. of Milwaukee  (incorporated by reference to
        Exhibit  2.1 of the  Company's  October 26, 1999 Form 8-K filed with the
        Securities and Exchange Commission on November 1, 1999).

2.2     Post-Closing  Indemnification  and Escrow  Agreement  in relation to the
        acquisition of Tricom,  Inc. of Milwaukee  (incorporated by reference to
        Exhibit  2.2 of the  Company's  October 26, 1999 Form 8-K filed with the
        Securities and Exchange Commission on November 1, 1999).

3.1     Amended and Restated  Articles of  Incorporation  of Wintrust  Financial
        Corporation  (incorporated  by reference to Exhibit 3.1 of the Company's
        Form S-1 Registration Statement (No 333-18699) filed with the Securities
        and Exchange Commission on December 24, 1996).

3.2     Statement of Resolution  Establishing  Series of Junior Serial Preferred
        Stock A of Wintrust Financial Corporation  (incorporated by reference to
        Exhibit 3.2 of the Company's  Form 10-K for the year ended  December 31,
        1998).

                                     - 28 -

3.3     Amended  By-laws of  Wintrust  Financial  Corporation  (incorporated  by
        reference  to Exhibit  3(i) of the  Company's  Form 10-Q for the quarter
        ended June 30, 1998).

4.1     Rights  Agreement  between Wintrust  Financial  Corporation and Illinois
        Stock  Transfer   Company,   as  Rights  Agent,   dated  July  28,  1998
        (incorporated  by  reference  to Exhibit 4.1 of the  Company's  Form 8-A
        Registration  Statement  (No.  000-21923)  filed with the Securities and
        Exchange Commission on August 28, 1998).

4.2     Preferred   Securities  Guarantee  Agreement  by  and  between  Wintrust
        Financial  Corporation and Wilmington  Trust Company dated September 29,
        1998,  relating to the 9.00%  Cumulative  Trust Preferred  Securities of
        Wintrust  Capital Trust I  (incorporated  by reference to Exhibit 4.2 of
        the Company's Form 10-K for the year ended December 31, 1998).

4.3     Indenture by and between Wintrust  Financial  Corporation and Wilmington
        Trust  Company  dated   September  29,  1998,   relating  to  the  9.00%
        Subordinated Debentures issued to Wintrust Capital Trust I (incorporated
        by  reference  to Exhibit  4.3 of the  Company's  Form 10-K for the year
        ended December 31, 1998).

4.4     Amended and Restated  Trust  Agreement by and among  Wintrust  Financial
        Corporation,  Wilmington Trust Company and the  Administrative  Trustees
        named therein dated September 29, 1998, relating to the 9.00% Cumulative
        Trust Preferred  Securities of Wintrust Capital Trust I (incorporated by
        reference to Exhibit 4.4 of the  Company's  Form 10-K for the year ended
        December 31, 1998).

4.5     Form of  Preferred  Security  Certificate  of Wintrust  Capital  Trust I
        (included as an exhibit to Exhibit 4.4).

4.6     Form of Subordinated Debenture (included as an exhibit to Exhibit 4.3).

10.1    $25 Million  Revolving Loan Agreement  between LaSalle National Bank and
        Wintrust Financial Corporation, dated September 1, 1996 (incorporated by
        reference  to  Exhibit  10.1  of the  Company's  Form  S-1  Registration
        Statement  (No.  333-18699)  filed  with  the  Securities  and  Exchange
        Commission on December 24, 1996).

10.2    First Amendment to Loan Agreement between Wintrust Financial Corporation
        and  LaSalle  National  Bank,  dated  March  1,  1997  (incorporated  by
        reference to Exhibit 10.29 to Registrant's  Form 10-K for the year ended
        December 31, 1996, filed with the Securities and Exchange  Commission on
        March 28, 1997).

10.3    Second   Amendment  to  Loan  Agreement   between   Wintrust   Financial
        Corporation and LaSalle National Bank, dated March 1, 1997 (incorporated
        by  reference to Exhibit  10.3 of the  Company's  Form 10-K for the year
        ended  December  31,  1997,  filed  with  the  Securities  and  Exchange
        Commission on March 31, 1998).

                                     - 29 -

10.4    Third Amendment to Loan Agreement between Wintrust Financial Corporation
        and LaSalle  National Bank,  dated  September 1, 1998  (incorporated  by
        reference to Exhibit 10 of the Company's Form 10-Q for the quarter ended
        September 30, 1998, filed with the Securities and Exchange Commission on
        November 13, 1998).

10.5    Fourth   Amendment  to  Loan  Agreement   between   Wintrust   Financial
        Corporation  and LaSalle Bank National  Association,  dated September 1,
        1999.

10.6    Form of Wintrust Financial  Corporation Warrant Agreement  (incorporated
        by reference to Exhibit  10.29 to Amendment No. 1 to  Registrant's  Form
        S-4 Registration Statement (No. 333-4645), filed with the Securities and
        Exchange Commission on July 22, 1996).*

10.7    Lake Forest Bank & Trust Company Lease for drive-up  facility located at
        the corner of Bank Lane & Wisconsin Avenue, Lake Forest, Illinois, dated
        December  11,  1992  (incorporated  by  reference  to  Exhibit  10.6  to
        Amendment No. 1 to  Registrant's  Form S-4  Registration  Statement (No.
        333-4645) filed with the Securities and Exchange  Commission on July 22,
        1996).

10.8    Lake Forest Bank & Trust Company Lease for banking  facility  located at
        810  South  Waukegan  Road,  Lake  Forest,   Illinois  (incorporated  by
        reference to Exhibit 10.6 to Amendment  No. 1 to  Registrant's  Form S-4
        Registration  Statement  (No.  333-4645)  filed with the  Securities and
        Exchange Commission on July 22, 1996).

10.9    Lake Forest Bank & Trust Company Lease for banking  facility  located at
        666 North Western Avenue, Lake Forest, Illinois, dated July 19, 1991 and
        Amendment  (incorporated by reference to Exhibit 10.6 to Amendment No. 1
        to Registrant's  Form S-4  Registration  Statement (No.  333-4645) filed
        with the Securities and Exchange Commission on July 22, 1996).

10.10   Lake Forest Bank & Trust Company Lease for banking  facility  located at
        103 East Scranton Avenue, Lake Bluff,  Illinois,  dated November 1, 1994
        (incorporated  by  reference  to  Exhibit  10.6 to  Amendment  No.  1 to
        Registrant's Form S-4 Registration  Statement (No.  333-4645) filed with
        the Securities and Exchange Commission on July 22, 1996).

10.11   North Shore Bank & Trust Company Lease for banking  facility  located at
        362 Park Avenue, Glencoe, Illinois, dated July 27, 1995 (incorporated by
        reference to Exhibit 10.6 to Amendment  No. 1 to  Registrant's  Form S-4
        Registration  Statement  (No.  333-4645)  filed with the  Securities and
        Exchange Commission on July 22, 1996).

                                     - 30 -

10.12   North Shore Bank & Trust Company Lease for banking  facility  located at
        794 Oak Street, Winnetka, Illinois, dated June 16, 1995 (incorporated by
        reference to Exhibit 10.6 to Amendment  No. 1 to  Registrant's  Form S-4
        Registration  Statement  (No.  333-4645)  filed with the  Securities and
        Exchange Commission on July 22, 1996).

10.13   Barrington  Bank and Trust  Company  Lease for property  located at 202A
        South  Cook  Street,  Barrington,  Illinois,  dated  December  29,  1995
        (incorporated  by reference to Exhibit 10.24 of the  Company's  Form S-1
        Registration  Statement (No  333-18699)  filed with the  Securities  and
        Exchange Commission on December 24, 1996).

10.14   Real Estate Contract by and between Wolfhoya Investments, Inc. and Amoco
        Oil Company,  dated March 25, 1996, and amended as of __________,  1996,
        relating  to the  purchase  of  property  located  at 201  South  Hough,
        Barrington,  Illinois (incorporated by reference to Exhibit 10.25 of the
        Company's Form S-1 Registration  Statement (No 333-18699) filed with the
        Securities and Exchange Commission on December 24, 1996).

10.15   Form of Employment Agreement entered into between the Company and Howard
        D. Adams,  former Chairman and Chief Executive Officer  (incorporated by
        reference  to  Exhibit  10.26 of the  Company's  Form  S-1  Registration
        Statement  (No.  333-18699)  filed  with  the  Securities  and  Exchange
        Commission on December 24, 1996). *

10.16   Form of  Employment  Agreement  (entered  into  between  the Company and
        Edward J. Wehmer,  President and Chief Executive  Officer).  The Company
        entered into Employment Agreements with David A. Dykstra, Executive Vice
        President and Chief  Financial  Officer,  Robert F. Key,  Executive Vice
        President-Marketing,     Lloyd     M.     Bowden,     Executive     Vice
        President-Technology    and   Randolph   M.   Hibben,   Executive   Vice
        President-Investments  during 1998 in  substantially  identical  form to
        this  exhibit  (incorporated  by  reference  to  Exhibit  10.15  of  the
        Company's Form 10-K for the year ended December 31, 1998). *

10.17   First Premium  Services,  Inc. Lease, as amended,  for corporate offices
        located  at  Lake  Cook  Road,  Deerfield,   Illinois  (incorporated  by
        reference to Exhibit 10.27 to Amendment No. 1 of the Company's  Form S-1
        Registration  Statement  (No.  333-18699)  filed with the Securities and
        Exchange Commission on January 24, 1997).

10.18   Lake Forest Bank & Trust Company Lease for drive-up and walk-up facility
        located  at 911 South  Telegraph  Road,  Lake  Forest,  Illinois,  dated
        November  7,  1996  (incorporated  by  reference  to  Exhibit  10.28  to
        Amendment No. 1 of the Company's  Form S-1  Registration  Statement (No.
        333-18699) filed with the Securities and Exchange  Commission on January
        24, 1997).

10.19   Wintrust  Financial  Corporation 1997 Stock Incentive Plan (incorporated
        by  reference to Appendix A of the Proxy  Statement  relating to the May
                         ----------
        22, 1997 Annual Meeting of Shareholders of the Company). *

                                     - 31 -

10.20   Wintrust   Financial    Corporation   Employee   Stock   Purchase   Plan
        (incorporated by reference to Appendix B of the Proxy Statement relating
                                      ----------
        to the May 22, 1997 Annual Meeting of Shareholders of the Company). *

13.1    1999 Annual Report to Shareholders.

21.1    Subsidiaries of the Registrant.

23.1    Consent of Independent Auditors.

27.1    Financial Data Schedule.

(b)     Reports on Form 8-K

        There were three Form 8-K reports filed with the Securities and Exchange
        Commission during the fourth quarter of 1999 as follows:

                October  19,  1999 - Form  8-K  filed  on  October  28,  1999 to
                announce the Company's third quarter 1999 earnings.

                October  26,  1999 - Form  8-K  filed  on  November  1,  1999 to
                announce the completion of the  acquisition  of Tricom,  Inc. of
                Milwaukee.

                December  23, 1999 - Form 8-K/A  filed on  December  23, 1999 to
                include  the  required   financial   statements  and  pro  forma
                financial  information in relation to the acquisition of Tricom,
                Inc. of Milwaukee.


                                     - 32 -

                                   SIGNATURES

Pursuant to the  requirements of Section 13 or 15(d) of the Securities  Exchange
Act of 1934,  the  registrant  has duly  caused  this report to be signed on its
behalf by the undersigned, thereunto duly authorized.

Wintrust Financial Corporation

Edward J. Wehmer            EDWARD J. WEHMER                      March 28, 2000
                            --------------------------
                            President and Chief Executive Officer

David A. Dykstra            DAVID A. DYKSTRA                      March 28, 2000
                            --------------------------
                            Executive Vice President &
                            Chief Financial Officer
                            (Principal Financial Officer)

Todd A. Gustafson           TODD A. GUSTAFSON                     March 28, 2000
                            --------------------------
                            Vice President - Finance
                            (Principal Accounting Officer)

Pursuant to the requirements of the Securities Exchange Act of 1934, this report
has been signed below by the following  persons on behalf of the  registrant and
in the capacities and on the dates indicated.

John S. Lillard             JOHN S. LILLARD                       March 28, 2000
                            --------------------------
                            Chairman of the Board of Directors

Edward J. Wehmer            EDWARD J. WEHMER                      March 28, 2000
                            --------------------------
                            President and CEO and Director

Joseph Alaimo               JOSEPH ALAIMO                         March 28, 2000
                            --------------------------
                            Director

Peter Crist                 PETER CRIST                           March 28, 2000
                            --------------------------
                            Director

Bruce K. Crowther           BRUCE K. CROWTHER                     March 28, 2000
                            --------------------------
                            Director

Maurice F. Dunne, Jr.       MAURICE F. DUNNE, JR.                 March 28, 2000
                            --------------------------
                            Director

William C. Graft            WILLIAM C. GRAFT                      March 28, 2000
                            --------------------------
                            Director

Kathleen R. Horne           KATHLEEN R. HORNE                     March 28, 2000
                            --------------------------
                            Director

                                     - 33 -


John Leopold                JOHN LEOPOLD                          March 28, 2000
                            --------------------------
                            Director

James E. Mahoney            JAMES E. MAHONEY                      March 28, 2000
                            --------------------------
                            Director

James B. McCarthy           JAMES B. MCCARTHY                     March 28, 2000
                            --------------------------
                            Director

Marquerite Savard McKenna   MARQUERITE SAVARD MCKENNA             March 28, 2000
                            --------------------------
                            Director

Albin F. Moschner           ALBIN F. MOSCHNER                     March 28, 2000
                            --------------------------
                            Director

Thomas J. Neis              THOMAS J. NEIS                        March 28, 2000
                            --------------------------
                            Director

Hollis W. Rademacher        HOLLIS W. RADEMACHER                  March 28, 2000
                            --------------------------
                            Director

J. Christopher Reyes        J. CHRISTOPHER REYES                  March 28, 2000
                            --------------------------
                            Director

Peter Rusin                 PETER RUSIN                           March 28, 2000
                            --------------------------
                            Director

John N. Schaper             JOHN N. SCHAPER                       March 28, 2000
                            --------------------------
                            Director

John J. Schornack           JOHN J. SCHORNACK                     March 28, 2000
                            --------------------------
                            Director

Ingrid S. Stafford          INGRID S. STAFFORD                    March 28, 2000
                            --------------------------
                            Director

Jane R. Stein               JANE R. STEIN                         March 28, 2000
                            --------------------------
                            Director

Katharine V. Sylvester      KATHARINE V. SYLVESTER                March 28, 2000
                            --------------------------
                            Director

Lemuel H. Tate, Jr.         LEMUEL H. TATE, JR.                   March 28, 2000
                            --------------------------
                            Director

Larry Wright                LARRY WRIGHT                          March 28, 2000
                            --------------------------
                            Director

                                     - 34 -