SCHEDULE 14A
(RULE 14A-101)

INFORMATION REQUIRED IN PROXY STATEMENT

SCHEDULE 14A INFORMATION
PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES
EXCHANGE ACT OF 1934 (AMENDMENT NO. )

Filed by the Registrant [X]

Filed by a Party other than the Registrant [ ]

Check the appropriate box:

[ ] Preliminary Proxy Statement [ ] Confidential, for Use of the Commission
Only (as permitted by Rule 14a-6(e)(2))
[X] Definitive Proxy Statement
[ ] Definitive Additional Materials
[ ] Soliciting Material Pursuant to Rule 14a-11(c) or Rule 14a-12

Cumberland Bancorp, Inc.
- --------------------------------------------------------------------------------
(Name of Registrant as Specified In Its Charter)

- --------------------------------------------------------------------------------
(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

[X] No fee required.

[ ] Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.

(1) Title of each class of securities to which transaction applies:

(2) Aggregate number of securities to which transaction applies:

(3) Per unit price or other underlying value of transaction computed
pursuant to Exchange Act Rule 0-11 (set forth the amount on which the
filing fee is calculated and state how it was determined):

(4) Proposed maximum aggregate value of transaction:

(5) Total fee paid:

[ ] Fee paid previously with preliminary materials:

[ ] Check box if any part of the fee is offset as provided by Exchange Act Rule
0-11(a)(2) and identify the filing for which the offsetting fee was paid
previously. Identify the previous filing by registration statement number,
or the Form or Schedule and the date of its filing.

(1) Amount Previously Paid:

(2) Form, Schedule or Registration Statement No.:

(3) Filing Party:

(4) Date Filed:
2

CUMBERLAND BANCORP, INC.

April 13, 2000

TO THE STOCKHOLDERS OF CUMBERLAND BANCORP, INC.:

In connection with the Annual Meeting of Stockholders of your Company to be held
April 27, 2000, we enclose a Notice of Annual Meeting of Stockholders, a proxy
statement, and a form of proxy.

The shareholders are being asked to elect the board of directors to serve until
the next Annual Meeting of Stockholders in 2001 or until successors are duly
elected and qualified, approve our 1998 Stock Option Plan as submitted in our
SEC filing in connection with our initial public offering, and to ratify the
appointment of Heathcott & Mullaly, as the Company's independent accountants and
auditors for fiscal year 2000. Information about these matters is contained in
the attached proxy statement.

You are invited to attend the Annual Meeting of shareholders in person and
should have recently received an invitation to this meeting. We would appreciate
your completing the enclosed form of proxy so that your shares can be voted in
the event that you are unable to attend the meeting. If you are present at the
meeting and desire to vote your shares personally, your form of proxy will be
withheld from voting upon your request prior to balloting. We urge you to return
your proxy card in the enclosed envelope as soon as possible.

Sincerely,

/s/ Joel Porter /s/ Tom Paschal
- ----------------------------------- -----------------------------------
Joel Porter Tom Paschal
President Secretary

Cumberland Bancorp, Inc.

4205 Hillsboro Road, Suite 101
Nashville, TN 37215

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS
TO BE HELD APRIL 27, 2000

The Annual Meeting of Shareholders of Cumberland Bancorp, Inc. will be
held at the Marriott Cool Springs, Convention Center, 700 Cool Springs Boulevard
East, Franklin, Tennessee, on Thursday, April 27, 2000 at 4:30 p. m., for the
following purposes:

1. To elect thirteen (13) directors to hold office until the next
Annual Meeting of Shareholders or until their successors are
elected and qualified;

2. To approve the 1998 Stock Option Plan for Cumberland Bancorp,
Inc.;

3. To ratify the appointment of Heathcott & Mullaly, P.C. as the
Company's independent accountants and auditors for fiscal year
2000; and

4. To transact such other business as may properly come before
the Annual Meeting or any adjournments thereof.

Only shareholders of record at the close of business on March 31, 2000 shall be
entitled to notice of and to vote at the Annual Meeting of Shareholders.

Your attention is directed to the Proxy Statement accompanying this notice for a
more complete statement regarding the matters proposed to be acted upon at the
Annual Meeting of the Shareholders.

By Order of the Board of Directors

/s/ Tom Paschal
--------------------------------------------
Tom E. Paschal, Secretary

April 13, 2000

IMPORTANT

PLEASE MARK, SIGN, DATE, INDICATE IF YOU PLAN TO ATTEND THE ANNUAL MEETING AND
RETURN THE ENCLOSED PROXY AS PROMPTLY AS POSSIBLE IN THE ENCLOSED ENVELOPE.
SHOULD YOU SUBSEQUENTLY DESIRE TO REMOVE YOUR PROXY, YOU MAY DO SO AS PROVIDED
IN THE ACCOMPANYING PROXY STATEMENT AT ANY TIME BEFORE IT IS VOTED.

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CUMBERLAND BANCORP, INC.

4205 Hillsboro Road, Suite 101
Nashville, TN 37215

PROXY STATEMENT

Annual Meeting of Shareholders
April 27, 2000

INTRODUCTION

This Proxy Statement is furnished in connection with the solicitation of proxies
to be used at the Annual Meeting of Shareholders (the "Annual Meeting"), of
Cumberland Bancorp, Inc. (the "Company") to be held on Thursday, April 27, 2000,
at 4:30 p.m., at the Marriott Cool Springs, Convention Center, 700 Cool Springs
Boulevard East, Franklin, Tennessee 37067 and any adjournments thereof.

AT THE ANNUAL MEETING, THE SHAREHOLDERS WILL VOTE TO ELECT A BOARD OF DIRECTORS,
TO APPROVE THE 1998 STOCK OPTION PLAN, AND TO RATIFY THE APPOINTMENT OF
HEATHCOTT & MULLALY, P.C. AS THE COMPANY'S INDEPENDENT AUDITORS FOR FISCAL 2000.
THE AFFIRMATIVE VOTE OF A MAJORITY OF THE SHARES PRESENT OR REPRESENTED AT THE
MEETING, IF A QUORUM EXISTS, IS REQUIRED TO ELECT THE DIRECTORS AND TO RATIFY
THE APPOINTMENT OF HEATHCOTT & MULLALY, P. C. AS THE COMPANY'S INDEPENDENT
AUDITORS FOR FISCAL 2000. THE HOLDER OF EACH SHARE OF THE COMPANY'S STOCK IS
ENTITLED TO ONE VOTE ON ALL MATTERS SUBMITTED BEFORE THE ANNUAL MEETING OR ANY
ADJOURNMENTS. THE PRESENCE IN PERSON OR BY PROXY OF THE HOLDERS OF A MAJORITY OF
THE ISSUED AND OUTSTANDING SHARES OF THE STOCK ENTITLED TO VOTE AT THE ANNUAL
MEETING IS NECESSARY TO CONSTITUTE A QUORUM.

Shareholders are urged to sign the enclosed form of proxy and return it promptly
in the envelope enclosed for that purpose. Proxies will be voted in accordance
with the stockholders' directions. If no directions are given, proxies will be
voted FOR the election of the proposed nominees named as directors, FOR the
approval of the 1998 Stock Option Plan, FOR the ratification of the appointment
of Heathcott & Mullaly, P. C. as the Company's independent auditors for fiscal
year 2000.

The Board of Directors knows of no other business to be presented at the Annual
Meeting. If any other business is properly presented, the person named in the
enclosed proxy will use his discretion in voting the shares. The proxy may be
revoked at any time prior to the voting thereof by written request to the
Company at 4205 Hillsboro Road, Suite 101, Nashville, TN 37215, Attention: Tom
Paschal, Secretary. The proxy may also be revoked by submission to the Company
of a more recently dated proxy. The giving of proxy will not affect the right of
a stockholder to attend the Annual Meeting and vote in person. If a stockholder
is present at the

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Annual Meeting and desires to vote his or her shares personally, the
stockholder's proxy will be withheld from voting upon request prior to
balloting.

The solicitation of proxies in the enclosed form is made on behalf of the Board
of Directors of the Company. The entire cost of the soliciting these proxies
will be borne by the Company. In addition to being solicited through the mails,
proxies may be solicited personally or by telephone facsimile by officers,
directors and employees of the Company who will receive no additional
compensation for such activities. Arrangements will also be made with brokerage
houses and other custodians, nominees and fiduciaries to forward solicitation
materials to the beneficial owners of shares held of record by such persons, who
will be reimbursed for their reasonable expenses incurred in such connection. It
is expected that this Proxy Statement will first be sent to shareholders on
April 13, 2000.

OUTSTANDING VOTING SHARES

Only stockholders of record on March 31, 2000 are entitled to notice of and to
vote at the Annual Meeting. On that date there were 6,876,597 shares of stock
issued and outstanding. The holder of each share of stock is entitled to one
vote on all matters submitted before the Annual Meeting or any adjournments of
the Annual Meeting.

INDEPENDENT ACCOUNTANTS

Heathcott & Mullaly, P. C. served as the independent accountants for the Company
during the year ended December 31, 1999. Representatives of Heathcott & Mullaly
P. C. will be present at the annual meeting and will be given the opportunity to
respond to questions.

PROPOSAL I
ELECTION OF DIRECTORS

The Company's directors are elected each annual meeting of the shareholders and
hold office until the next election of directors or until their successors are
duly elected and qualified. The Company's by-laws provide for a minimum of three
and a maximum of fifteen directors, the exact number to be set by the Board of
Directors. The thirteen persons named below, all of whom currently serve as
directors of the Company, have been nominated for election to serve until the
2001 Annual Meeting of Shareholders. The following table sets forth certain
information respecting the persons nominated to be directors of the Company,
which has been furnished to the Company by the individuals named:

Name Age Position
---- --- --------

DIRECTORS
Joel Porter (1)(2) .......... 59 President (our Principal Executive Officer);
Director

John S. (Jack) Everett (1)(2) 60 President of BankTennessee; Director

Danny Herron (1)(2) ......... 42 President of The Community Bank; Director

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Tom E. Paschal (1)(2) ....... 54 Secretary; President of Cumberland Bank;
Director

John S. Wilder, Sr. (1) ..... 79 Chairman of our Board

Tom Brooks .................. 71 Director

Jerry Cole .................. 68 Director

Frank Inman, Jr(1) .......... 63 Director

Alex Richmond(3) ............ 50 Director

Wayne Rodgers ............... 60 Director; Executive Vice President of
BankTennessee
John S. Shepherd ............ 63 Director
William D. Smallwood ........ 48 Director, President Bank of Dyer
Ronald Gibson ............... 40 Director, President The Murray Bank

DIRECTOR EMERITUS

Herman W. Cox, Jr ........... 77 Director Emeritus

- ----------

(1) Member of executive committee
(2) Member of management committee
(3) Member of audit committee along with Chairman Dr. Eugene Smith and
Mr. Tom Price.

There are no family relationships between any of our executive officers.

Joel Porter has served as our president since our formation, although
he does not devote his full time to that position and is not compensated for his
services as president. Mr. Porter is a named partner of the law firm of Burch,
Porter & Johnson, PLLC, located in Memphis, where he has practiced since 1964.
Mr. Porter is also the president of two finance and investment firms, Porter
Development and Porter Investment. Mr. Porter has served as a member of our
board of directors since 1986. He has also served as a director and board
chairman of BankTennessee since 1992, a director of Cumberland Bank since 1986,
a director of The Community Bank since 1992, and a director of The Murray Bank
since June 1999.

John S. Everett has served as the president of BankTennessee in
Collierville since February 1992. Mr. Everett has served as a director of The
Community Bank since 1993 and is that boards chairman. Mr. Everett has also
served as a director of Cumberland Bank since 1986, BankTennessee since 1992,
and The Murray Bank since June 1999. He has served as one of our directors since
1992.

Danny Herron has served as president of The Community Bank since 1993.
Mr. Herron has served as a director of The Community Bank since 1993, and as one
of our directors since 1997.

Tom Paschal has served as the president and chief executive officer of
Cumberland Bank since 1986. He has also served as our secretary since 1991. Mr.
Paschal has served as a director of Cumberland Bank since 1990, a director of
Cumberland Finance since 1995, a director of CBC Financial Services since 1995,
and as one of our directors since 1990.

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John S. Wilder has served as a member of our board of directors since
1992 and is currently our Chairman of the Board. Mr. Wilder has served as the
Lieutenant Governor of the State of Tennessee since 1971, and is the longest
sitting Lieutenant Governor of any state in United States history. Mr. Wilder
also serves as a director of the Cumberland Bank, The Community Bank, The Murray
Bank and of BankTennessee. He serves as a director of United Foods, Inc. and as
a member of its compensation committee. Mr. Wilder is a director and part owner
of Health Management, Inc., a waste disposal firm in Somerville, Tennessee. Mr.
Wilder is also a partner of Longtown Farms, a farming business in Mason,
Tennessee, and a Vice President and part-owner of Longtown Supply, Inc., a
service station and farming supply business in Mason, Tennessee.

Tom Brooks has served on our board of directors since July 1997. Mr.
Brooks retired from work as a pharmacist at Brooks Pharmacy, a Super D franchise
he owned in Collierville until 1996. Mr. Brooks served as vice mayor and
alderman of Collierville from 1975 to 1999, and was a member of its planning
commission from 1959 to 1999. Mr. Brooks also serves as a director of
BankTennessee where he has served since 1992.

Jerry Cole has served as one of our directors since 1995. Mr. Cole
retired from the Agriculture Department of the University of Tennessee in 1994
where he had served as an extension agent for the previous thirty-two (32)
years. Mr. Cole has served on the board of directors of Cumberland Bank since
1990 where he currently serves as that board's chairman. Mr. Cole has served as
a director of Cumberland Finance since 1995.

Frank Inman, Jr. has served on our board of directors since 1991. Mr.
Inman is the president and chairman of the board of directors of Inman
Construction Corp., a general contractor, a position he has held since 1970. Mr.
Inman has also served as a director of Cumberland Bank since 1986.

Alex Richmond has served as a director on our board of directors since
1990. Mr. Richmond has been a grocer for many years, and has owned two grocery
stores, G&R, Inc. and D.A.G. Foods, since 1991. Mr. Richmond serves as president
of G&R, Inc. and president of Consolidated Investors, a small business
investment firm. Mr. Richmond is a partner in Richmond & Franklin, a real estate
investment company, and is the owner of Richco, Inc., a Tennessee company that
operates primarily as a purchaser of grocery stores. He has served as a director
of Cumberland Bank since 1990.

Wayne Rodgers has served as the executive vice president of
BankTennessee since 1992 and was appointed in June 1999 to serve as a director
on our board. He is responsible for overseeing the lending function and retail
branches of the bank. He also is the supervisor of the SBA lending program for
the bank. Mr. Rodgers serves on the loan, audit, asset and liability management
and CRA/compliance committees of the bank. He has been a director of
BankTennessee since 1992.

John S. Shepherd has been a member of our board of directors since July
1997. Since 1993, Mr. Shepherd has been self-employed engaged principally in
investing and as a merchant in Collierville, Tennessee. Mr. Shepherd has been a
member of the Memphis/Shelby County Board of Adjustment since 1972 and its
chairman since 1996. Mr. Shepherd has served as a director of BankTennessee
since 1992 and The Murray Bank since June 1999.

William D. Smallwood has served as the President of Bank of Dyer since
1983 and has served as a board member there since that time. He was appointed to
the board in January, 2000 upon completion of the merge.

Ronald Gibson has served as President of The Murray Bank since June,
1999 when the bank opened for business and he has served as a board member there
since that date. Mr. Gibson was appointed to the Company Board in September,
1999.

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Herman W. Cox, Jr served on our board of directors beginning July of
1997 and is a non-voting director emeritus. Mr. Cox owns and operates McGinnis
Oil Co., a gasoline distributor in Collierville, Tennessee, a business he has
operated since 1939. Mr. Cox has served on the board of directors of
BankTennessee since 1992. Mr. Cox served as mayor from 1975 to 1999 and was a
member of the board of aldermen from 1959 to 1999. Mr. Cox is the father of
Herman W. Cox III.

THE BOARD OF DIRECTORS RECOMMENDS VOTING FOR APPROVAL OF THESE NOMINATED PERSONS
TO SERVE AS THE BOARD OF THE COMPANY.

MEETINGS AND COMMITTEES OF THE BOARD OF DIRECTORS

Our board of directors and the board of directors of our banks operate
through several standing committees. Below is a description of each relevant
committee indicating members of each committee and the frequency with which each
committee meets.

Executive Committee. The executive committee is charged with the review
of corporate matters presented, or to be presented, to our board of directors,
making recommendations to the board of directors on policy matters and making
executive decisions on matters that do not require a meeting of the full board
of directors. Review of expansion possibilities and corporate opportunities as
well as oversight of general corporate governance matters are the chief
functions of our executive committee. The executive committee held four meetings
during 1999.

Management Committee. The management committee is charged with the
review of banking matters presented, or to be presented, to our board of
directors, making recommendations to our board of directors on policy matters at
our bank subsidiaries' level and making executive decisions on matters that do
not require a meeting of the full board of directors. Our management committee
focuses on our and our bank and non-bank subsidiaries' operations, including
management of personnel matters and financial results. The management committee
was formed in March 1999 and held three meetings during the year.

Audit Committee of Company. The audit committee reviews our accounting
practices and procedures, as well as the scope of our audit. Additionally, the
committee assists in the recommendation of the appointment of our independent
auditors. The audit committee was formed in March 1999, and held four meetings
during the year.

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EXECUTIVE COMPENSATION

The following table sets forth summary information concerning the
compensation we paid for services rendered to us during 1997, 1998 and 1999, by
our Chief Executive Officer and our other four most highly compensated executive
officers who were serving as executive officers at the end of 1999 and whose
salaries were in excess of $100,000 in 1999. We do not have a designated Chief
Executive Officer. Joel Porter is our president and is considered our principal
executive officer. However, Mr. Porter receives no compensation as president and
receives compensation only for his service as a director or committee member of
the executive committee.

SUMMARY COMPENSATION TABLE

LONG-TERM
COMPENSATION
ANNUAL COMPENSATION AWARDS

SECURITIES
FISCAL OTHER ANNUAL ALL OTHER UNDERLYING
NAME AND PRINCIPAL POSITION YEAR SALARY($) BONUS($) COMPENSATION($)(1) COMPENSATION ($)(2) OPTIONS
--------------------------- ---- --------- -------- ------------------ ------------------- -------

John S. Jack Everett........... 1999 161,000 28,000 -- 44,000 13,750
President of BankTennessee 1998 153,000 28,000 -- 45,000 13,750
1997 140,000 15,000 -- 43,000 --

Tom Paschal.................... 1999 135,000 42,000 -- 29,000 13,750
President of Cumberland 1998 110,000 24,000 -- 30,000 13,750
Bank, and Secretary 1997 90,000 18,000 -- 25,000 --

Danny Herron................... 1999 100,000 -- -- 15,000 13,750
President of The Community 1998 90,000 10,000 -- 17,000 13,750
Bank 1997 85,000 10,000 -- 10,000 --

Wayne Rodgers.................. 1999 115,000 10,000 -- 6,000 13,750
Executive Vice President 1998 109,000 9,000 -- 6,000 13,750
of BankTennessee 1997 100,000 10,000 -- 5,000 --

William Smallwood.............. 1999 139,000 3,000 -- 2,000 --
President of Bank of Dyer 1998 138,000 5,000 -- 2,000 --
1997 120,000 4,000 -- 2,000 --

(1) Does not include prerequisites and other personal benefits paid to our
executive officers, which totaled less than 10% of the total salary and bonus
reported for the years indicated.
(2) Represents matching contributions to our 401(k) plan, benefits derived from
our payments for term life insurance for our officers, and directors fees
received by each individual. The amount of such benefits for 1998 is set forth
in the following table:

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TERM LIFE
401(K) PLAN INSURANCE DIRECTORS FEES
- ---------------------------------------------------------------------------

Jack Everett 5,000 2,000 37,000
- ---------------------------------------------------------------------------
Tom Paschal 5,000 5,000 19,000
- ---------------------------------------------------------------------------
Danny Herron 3,000 0 12,000
- ---------------------------------------------------------------------------
Wayne Rodgers 3,000 0 3,000
- ---------------------------------------------------------------------------
William Smallwood 0 0 2,000
- ---------------------------------------------------------------------------

COMPENSATION OF DIRECTORS

All of our directors receive a directors fee of $1,000 for each board
meeting attended and $1,000 for each committee meeting attended. Persons serving
as directors for any of our Banks who are not also employees of that bank,
receive additional compensation for each bank board and committee meeting
attended. In addition, each person who serves as chairman of a bank board of
directors, committee, or our board receives twice the compensation of other
members for each meeting attended. Directors are reimbursed for their expenses
incurred in connection with their activities as our directors.

1998 STOCK OPTION PLAN

We adopted the 1998 Stock Option Plan in March 1998. The purpose of the
plan is to attract, retain and reward directors, officers, and key employees by
offering equity interest in our company. Currently, all directors and employees
are eligible to participate in the 1998 plan. The plan provides for the grants
of nonqualified stock options. Nonqualified stock options are stock options
which do not constitute "incentive stock options" within the meaning of Section
422A of the Internal Revenue Code.

Our board of directors authorized a total of 550,000 shares of common
stock for issuance under the 1998 plan, adjusted to incorporate the recent 10%
stock dividend. As of December 31, 1999, we have granted options for the
purchase of 425,635 shares of common stock to employees and directors. The
number of shares granted under each option is adjusted for any stock dividends
or stock splits authorized by the board of directors.

ISSUANCE OF COMPANY OPTIONS

The following table sets forth key information with respect to the
grant of stock options under our 1998 Stock Option Plan. 20% of the options
granted in 1998 were earned and have became exercisable by directors, officers,
and employees, including those identified below, for the year ended December 31,
1999. No additional option grants were made in 1999 to persons who had received
options in 1998. During 1999, newly hired bank officers were granted an
additional 42,750 individual options. Also during 1999, 1,200 individual options
were exercised and 9,625 options were forfeited. (Refer to Note 20 of the
Company's Outside Audit contained in the 1999 Annual Report for additional
information)

EMPLOYMENT CONTRACTS, TERMINATION OF EMPLOYMENT AND CHANGE IN CONTROL
ARRANGEMENTS

None of our executive officers or other officers has an employment
contract.

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COMPENSATION COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION

Our Board of Directors serves as our compensation committee.
Compensation decisions are made by the full Board of Directors based upon
recommendations of the management of each of our Banks. Our Board of Directors
of each of our Banks determines independently compensation decisions for our
Banks' presidents. No interlocking relationship exists between our Board of
Directors (or management) and the Board of Directors or compensation committee
of any other company, nor has any interlocking relationship existed in the past.

REPORT ON EXECUTIVE COMPENSATION

The Company does not have a compensation committee. Decisions with
respect to compensation of the Company's and each of the Banks' executive
officers, including the Chief Executive Officer and the other named executive
officers, for fiscal 1999 were made by the Board of Directors of each of the
Banks. Compensation of executive officers consists of a base salary, an annual
bonus, matching contributions under the Company's 401(k) plan, and payments for
term life insurance (as well as health and disability insurance and other
non-cash benefits similar to those of all employees of the Banks or Company).
Mr. Porter, our president and principal executive officer, receives no
compensation other than as a director and for his services as a member of the
executive committee.

The overarching policy of each of the Board of Directors in determining
executive compensation is to attract and retain the highest quality talent to
lead the Banks and the Company and to reward key executives based upon their
individual performance and the performance of the Banks and the Company. Each of
the Board of Directors believes that providing incentives to, and rewarding the
performance of, officers enhances the profitability of Banks and the Company.

In recommending the 1999 base salary of each Bank's presidents and
other named executive officers, the Company and each of the Board of Directors
reviewed the 1999 financial performance of each Bank compared to past
performance. Each Bank president's salary was tied to the specific performance
of his Bank during 1999.

Executive officers were eligible for, and received, a cash bonus as
determined by the Board of Directors based upon the Company and each Bank's
overall financial performance. No specific quantitative performance measure (of
the Company, and of the Banks or any individual) was used to determine the
amount of bonus awarded. Instead, bonuses for executive officers were given in a
manner similar to the bonuses granted to all full-time employees of the banks or
the Company, with the amount awarded being most closely tied to the employee's
monthly salary.

The Board of Directors of Cumberland Bancorp, Inc. April 2000

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SHAREHOLDER RETURN PERFORMANCE GRAPH

The following graph compares the percentage change in the
unaudited total return on the Company's Common Stock against the cumulative
total return of the Nasdaq Index and The Carson Medlin Company's Independent
Bank Index between October 14, 1999 (soon after the Company became publicly
traded) and December 31, 1999. The graph assumes the value of the investment in
the Company's Common Stock and each index was $100 at October 14, 1999 and that
all dividends were reinvested.

CUMBERLAND BANCORP, INC.

[CHART]

PERIOD
ENDING
INDEX 10/14/99 10/31/99 11/30/99 12/31/99

Cumberland Bancorp, Inc. 100.00 100.00 100.00 100.00
NASDAQ - Total US* 100.00 105.77 118.13 144.56
SNL $500M-$1B Bank Index 100.00 102.30 102.45 96.30

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CERTAIN RELATIONSHIP AND RELATED TRANSACTIONS

We have, and expect to have in the future, banking and other business
transactions in the ordinary course of our banking business with our directors,
officers, and 5% beneficial owners and their affiliates, including members of
their families or corporations, partnerships, or other organizations in which
our officers or directors have a controlling interest, on substantially the same
terms (including price, or interest rates and collateral) as those prevailing at
the time for comparable transactions with unrelated parties. Any of these
banking transactions will not involve more than the normal risk of
collectability nor present other unfavorable features to us. At December 31,
1999, the outstanding principal amount of indebtedness of these loans, including
amounts available under lines of credit to our affiliates aggregated $3,931,000.

We believe that all of these transactions were made on terms as
favorable to us as transactions we have with other customers of the banks. We
also believe that our bank loan approval process for loans to officers and
directors was no different than the loan approval processes for other customers
of our banks.

CERTAIN OTHER TRANSACTIONS AND BUSINESS RELATIONSHIPS

Mr. Frank Inman, one of our directors, owns and operates Inman
Construction Company, which has been chosen as general contractor of our new
Collierville main office. Construction of the building is on a "cost plus" basis
and an expected price of approximately $2.7 million. Inman Construction Company
will employ Everett Construction Company as a sub-contractor for the project.
Everett Construction Company is owned by Mr. Greg Everett and Mr. John Everett,
sons of Mr. Jack Everett, one of our directors and president of BankTennessee.
An outside evaluation was obtained for the fair market cost of this project.
This evaluation was furnished to the TDFI and Federal Reserve, who have approval
authority over this transaction. The BankTennessee board and our board have
approved this transaction.

We have entered into a lease-purchase agreement for property in
Lafayette, Macon County, Tennessee, on which to locate our new Cumberland Bank
branch. Two of our directors, Mr. Tom Paschal and Mr. Alex Richmond, each own a
twenty percent (20%) interest in the property. The agreement contemplates
Cumberland Bank entering into a lease not to exceed $2,800 per month, and
retaining an option to purchase the property for $250,000. Cumberland Bank
retained an independent licensed real estate appraiser that performed an
evaluation of the property and lease terms to market comparable prices and lease
terms and found the property and the terms to fall within market comparables.
The transaction was consummated June 29, 1999. Our board and the Cumberland Bank
board have reviewed and approved the transaction. The appraiser evaluation along
with the bank branch application have been filed with the TDFI and the Federal
Reserve Bank of Atlanta.

We have employed Mr. Joel Porter's law firm, Burch, Porter & Johnson,
PLLC, from time to time. Fees and expenses arose out of general corporate and
other ordinary course of business services provided by Burch Porter, and account
for significantly less than one percent (1%) of the law firm's 1999 gross
revenue.

We believe that the above transactions were made on terms as favorable
to us as we would have received from unaffiliated third parties.

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PRINCIPAL SHAREHOLDERS

The following table sets forth, as of March 31, 2000, certain
information with respect to the beneficial ownership of our common stock held by
directors, executive officers, and each person known to our management to own
beneficially, directly, or indirectly, more than five percent (5%) of our
shares, and all directors and executive officers as a group. Except as otherwise
indicated, the shareholders listed in the table have sole voting and investment
power with respect to all our shares shown as beneficially owned by them. The
address of all the beneficial owners listed is 4205 Hillsboro Road, Suite 212,
Nashville, Tennessee 37215.

The percentage ownership in the table below is based on 6,876,597
shares outstanding as of March 31, 2000. Shares of common stock subject to
options currently exercisable or exercisable within 60 days of March 31, 2000
are deemed outstanding for the purpose of computing the percentage ownership of
the person holding the options but are not deemed outstanding for computing the
percentage ownership of any other person. Unless otherwise indicated below, the
persons and entities named in the table have sole voting and sole investment
power with respect to all shares beneficially owned.

Number of Shares
Beneficially
Owned as a Result
of Options
Currently
Number of Exercisable or
Shares Exercisable Within Percentage
Beneficially 60 Days of March 31, of Shares
Name of Beneficial Owner Owned 2000 Outstanding

Joel Porter ................. 895,347(1) 3,300 13.0
John Wilder ................. 713,591(2) 3,300 10.3
Jack Everett ................ 217,436(3) 5,500 3.2
Tom Brooks .................. 198,019 5,500 2.9
Jerry Cole .................. 47,566 3,300 *
Herman W. Cox, Jr ........... 46,714 5,500 *
Danny Herron ................ 35,750 5,500 *
Frank Inman ................. 159,623(4) 3,300 2.3
Tom Paschal ................. 101,816 5,500 1.5
Alex Richmond ............... 74,800(5) 3,300 1.1
Wayne Rodgers ............... 63,878 5,500 *
John Shepherd ............... 255,103 3,300 4.5
Mark McDowell ............... 74,195(6) 2,200 1.1
Ronnie Gibson ............... 8,333 0 *
Bill Smallwood .............. 171,304 0 2.5

All executive officers and
directors as a group 3,063,475 55,000 42.4
(15 persons)

- ----------
*Less than one percent
(1) Includes 1,292 shares held by Mr. Porter as trustee for his daughter.
(2) Includes 395,996 shares held by Mr. Wilder's spouse.
(3) Includes 127,111 shares held by Mr. Everett's spouse and 1,600 shares held
by Mr. Everett's 2 daughters.
(4) Includes 43,397 shares held by Mr. Inman's spouse.
(5) Includes 34,590 shares held by Mr. Richmond's spouse and 5,500
shares held by Mr. Richmond as custodian for his son.
(6) Includes 898 shares held by the two son's of Mr. McDowell.

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PROPOSAL II

APPROVAL OF THE 1998 STOCK OPTION PLAN

The second proposal is to approve the 1998 Stock Option Plan for
Cumberland Bancorp, Inc.

The stock option plan was adopted in March 1998 by the board of
directors. The purpose of the plan is to attract, retain and reward directors,
officers and key employees by offering equity interest in our company.
Currently, all directors and employees are eligible to participate in the 1998
plan. The plan provides for the grants of nonqualified stock options and
incentive stock options. Nonqualified stock options are stock options which do
not constitute "incentive stock options" within the meaning of Section 422A of
the Internal Revenue Code. At this time, we have granted, and expect to grant,
only nonqualified stock options.

The plan calls for the term and vesting period for each option granted
to be set by the plan's committee except that no option can vest prior to the
first anniversary of the grant date and no incentive stock option can be
exercised more than ten years, or for ten percent shareholders more than five
years, after the grant date. As a matter of practice, option granted under the
plan generally become exercisable at a rate of 20% per year until fully vested
in five years and then expire after an additional year. Under the plan, the
exercise price per share of option is set by the plan's committee and can not be
less than 50% of the market value of the shares at grant date. To date, the
exercise price of all options granted has been equal to the market value of the
shares at grant date, to the extent that such a value is considering the
historically limited market in our stock.

Our board of directors authorized a total of 550,000 shares of common
stock for issuance under our plan, adjusted to incorporate the March 26, 1999
10% stock dividend. Effective March 1, 1998, we granted employees and directors
options to purchase 393,710 shares under our plan at an exercise price of $5.45
per share. In 1999, we granted options to purchase 42,750 shares to twelve (12)
employees at an exercise price of $12.50 per share. As of December 31, 1999,
425,635 shares of common stock remain outstanding under the plan, after
forfeiture of 9,625 shares by person no longer employed by us or our Banks. The
number of shares granted under, and the exercise price per share of, each option
is adjusted to incorporate the March 26, 1999 10% stock dividend authorized by
our board of directors. The consummation of this offering does not accelerate or
otherwise affect the vesting of options under our plan and will not affect the
number of shares underlying the option granted. The adoption of this plan does
not accelerate or otherwise affect the vesting of options under the 1998 plan
and will not affect the number of shares underlying the options granted.

The 1998 Stock Option Plan is a public document available under the
Company's Registration Statement on Form S-1/A and is available for viewing on
the EDGAR database at www.sec.gov. You may also request a complimentary copy of
the 1998 plan from Mr. Paschal at our Company's main office.

THE BOARD OF DIRECTORS RECOMMENDS VOTING FOR APPROVAL OF THE PLAN.

14
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PROPOSAL III

RATIFICATION OF THE APPOINTMENT OF
HEATHCOTT & MULLALY, P. C. AS THE COMPANY'S INDEPENDENT
ACCOUNTANTS FOR FISCAL YEAR 2000

The Board of Directors has confirmed the appointment by the Audit
Committee of Heathcott & Mullaly, P. C. as the Company's independent accountants
for fiscal 2000. Heathcott & Mullaly P. C. served as independent accountants of
the Company for the years ended 1999, and 1998. A representative(s) of the firm
will be present at the Annual Meeting and will have an opportunity to make a
statement if they so desire and is expected to be available to respond to
appropriate questions.

The affirmative vote of the holders of a majority of the outstanding
shares of entitled to vote at the Annual Meeting is required to ratify the
appointment of Heathcott & Mullaly, P. C. as the Company's independent
accountants for fiscal year 2000.

THE BOARD OF DIRECTORS RECOMMENDS VOTING FOR RATIFICATION OF THE
APPOINTMENT OF HEATHCOTT & MULLALY, P. C. AS THE COMPANY'S INDEPENDENT
ACCOUNTANTS FOR FISCAL YEAR 2000.

OTHER MATTERS

The Board of Directors, at the time of preparation of this Proxy
Statement, knows of no business to come before the meeting other than that
referred to herein. If any other business should come before the meeting, the
persons named in the enclosed Proxy will have discretionary authority to vote
all proxies in accordance with their best judgement.

SECTION 16(A) BENEFICIAL OWNERSHIP REPORTING

The federal securities laws require the Company's directors, executive
officers and persons who beneficially own more than 10% of a registered class of
the Company's equity securities, to file with the Securities and Exchange
Commission initial report of ownership and reports of changes in ownership of
any securities of the Company. Joel Porter and John S. Wilder, Sr., owned more
than ten percent (10%) of the outstanding shares of common stock as of December
31, 1999. Additionally, SEC regulations require the Company to identify in its
Proxy Statement those individuals for whom one of the referenced reports was not
filed on a timely basis during the most recent fiscal year. Each of the
directors and executive officers was required to file a Form 3 (Initial
Statement of Beneficial Ownership of Securities) with the SEC contemporaneous
with the completion of the Company's initial public offering. In addition, new
directors are also required to file a Form 3. The required filings on the two
new directors, Mssrs. Gibson and Smallwood, were not timely made, but were made
in April 2000. Each of the directors and executive officers was required to file
a Form 4 (Statement of Changes of Beneficial Ownership of Securities) 10 days
following the month-end after a non-exempt transaction has occurred. Required
filings on Forms 4 each for one time transactions occurring during and after the
initial public offering of Mssrs. Cole,

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17

Everett, Gibson, Porter, McDowell, Smallwood, and Wilder, were not timely made,
but were all made in April 2000.

Each of the directors and officers was required to file a Form 5
(Annual Statement of Beneficial Ownership of Securities) after the year ending
December 31, 1999. The required filings of the above-listed non-exempt
individuals were not timely made, but were all made in April 2000.

PRINCIPAL SHAREHOLDERS

Joel Porter, and John S. Wilder, Sr. are the shareholders who, as of
the record date, owned more than five percent of the outstanding stock. Their
ownership is shown under "Election of Directors", to which reference is made for
details of his direct and indirect ownership.

SHAREHOLDER PROPOSALS

Proposals by shareholders to be considered for inclusion in the proxy
materials solicited by the Board of Directors for the annual meeting of
shareholders in 2001 must be received by Tom Paschal, Corporate Secretary,
Cumberland Bancorp, Inc., 4205 Hillsboro Road, Suite 101, Nashville, TN 37215 no
later than November 21, 2000. The use of Certified Mail - Return Receipt
Requested is advised. To be eligible for inclusion, a proposal must also comply
with Rule 14a-8 and all other applicable provisions of Regulation 14A under the
Securities Exchange Act of 1934.

For any other shareholder proposals to be timely (but not considered
for inclusion in the Company's Proxy Statement), a shareholder must forward such
proposal to Mr. Paschal at the Company's main office (listed above) no later
than February 26, 2001.

BY ORDER OF THE BOARD OF DIRECTORS

Nashville, Tennessee
April 10, 2000 Tom Paschal, Secretary

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18

REVOCABLE PROXY CUMBERLAND BANCORP, INC.

This proxy is solicited upon behalf of the Board of Directors for the Annual
Meeting to be held on April 27, 2000.

The undersigned hereby appoints Tom E. Paschal and Joel Porter, or either of
them, with full power of substitution, as proxies, and hereby authorizes them to
vote, as designated, all shares of common stock of Cumberland Bancorp, Inc.
held by the undersigned on March 31, 2000 at the Annual Meeting of the
Shareholders to be held Thursday, April 27, 2000 at 4:30 p.m., (CST) at the
Marriott Cool Springs, Convention Center, 700 Cool Springs Boulevard East,
Franklin, Tennessee 37067, and any adjournment(s) thereof.

1. THE ELECTION OF DIRECTORS:

Tom Brooks, Jerry Cole, Jack Everett, Ronnie Gibson, Danny Herron,
Frank Inman, Jr., Tom E. Paschal, Joel Porter, Alex Richmond, Wayne
Rodgers, John Shepherd, Bill Smallwood, John S. Wilder, Sr.

[ ] FOR all nominees listed above [ ] WITHHOLD AUTHORITY to
(except as marked to the vote for all 13
contrary below) nominees

[ ] Vote to withhold for the following nominee(s)
(write that nominee's name below.)

---------------------------------------------------------------

2. APPROVAL OF 1998 STOCK OPTION PLAN
[ ] FOR [ ] AGAINST [ ] ABSTAIN

3. RATIFICATION OF HEATHCOTT & MULLALY, P.C. AS INDEPENDENT AUDITORS
FOR THE CURRENT FISCAL YEAR.
[ ] FOR [ ] AGAINST [ ] ABSTAIN

In their discretion, the proxies are authorized to vote upon such
business as may properly come before this meeting.

CUMBERLAND BANCORP, INC.
4205 Hillsboro Road, Suite 101
Nashville, Tennessee 37215

Revocable Proxy for the
Annual Meeting of Shareholders
April 27, 2000

The undersigned hereby constitutes and appoints Tom E. Paschal and Joel Porter,
and each of them, the proxies of the undersigned, with full power of
substitution, to attend the Annual Meeting of Shareholders of Cumberland
Bancorp., Inc. (the "Company") to be held at the Marriott Cool Springs
Convention Center, 700 Cool Springs Boulevard East, Franklin, Tennessee 37067 on
Thursday, April 27, 2000 at 4:30 p.m., local time, and any adjournments thereof,
and to vote all the shares of stock of the Company that the undersigned may be
entitled to vote, upon the following matters.

DETACH PROXY CARD HERE
- --------------------------------------------------------------------------------

THIS PROXY IS SOLICITED BY THE BOARD OF DIRECTORS OF THE COMPANY, WILL BE VOTED
IN ACCORDANCE WITH THE INSTRUCTIONS MARKED HEREIN, AND WILL BE VOTED FOR
PROPOSALS 1, 2 AND 3 AND AS DETERMINED BY A MAJORITY OF THE BOARD OF DIRECTORS
AS TO OTHER MATTERS, IF NO INSTRUCTIONS TO THE CONTRARY ARE MARKED HEREIN AND
TO THE EXTENT THIS PROXY CONFERS DISCRETIONARY AUTHORITY.

Date
-----------------------

Signature
-------------------

Please mark, date and sign as your name appears herein and return in the
enclosed envelope. If acting as executor, administrator, trustee, guardian, etc,
you should so indicate with signing. If the signer is a corporation, please
sign the full name by duly appointed officer. If a partnership, please sign in
partnership name by authorized person. If shares are held jointly, each
shareholder named should sign.