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


                                    FORM 8-K


                 CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d)
                     OF THE SECURITIES EXCHANGE ACT OF 1934


       Date of Report (Date of Earliest Event Reported): January 27, 2000


                         WINTRUST FINANCIAL CORPORATION
             (Exact Name of Registrant as Specified in its Charter)


                         Commission File Number 0-21923


          Illinois                                       36-3873352
- -----------------------------               ------------------------------------
(State or other Jurisdiction                (I.R.S. Employer Identification No.)
    of Incorporation)




                               727 North Bank Lane
                           Lake Forest, Illinois 60045
             -------------------------------------------------------
                    (Address of Principal Executive Offices)


                                 (847) 615-4096
      ---------------------------------------------------------------------
              (Registrant's Telephone Number, Including Area Code)

ITEM 5.  OTHER EVENTS.

On January 27, 2000, Wintrust Financial  Corporation  ("Company") announced that
its Board of  Directors  approved  its first  semi-annual  cash  dividend in the
amount of $0.05 per share of outstanding  common stock.  The dividend is payable
on February 24, 2000 to shareholders of record as of February 10, 2000.

Additionally,   the  Board  of  Directors   approved  a  stock  buyback  program
authorizing the purchase of up to 300,000 shares of the Company's  common stock,
from time to time,  in open market or  privately  negotiated  transactions.  The
shares authorized to be repurchased represent  approximately 3% of the Company's
currently  outstanding  common  shares.  Shares  repurchased,  if any,  would be
available for issuance under the Company's stock incentive plan,  employee stock
purchase plan and other corporate purposes.


ITEM 7.  FINANCIAL STATEMENTS AND EXHIBITS.

(c)      Exhibit

Exhibit 99 - Press Release dated January 27, 2000.

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                                   SIGNATURES

Pursuant  to the  requirements  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
                                  (Registrant)


Date:  February 11, 2000                     /s/ David A. Dykstra
                                             --------------------
                                             Executive Vice President
                                             & Chief Financial Officer

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