Wintrust Financial Corporation Watch

from 8-K 36 pages Wintrust Financial Corporation (An Illinois Corporation) 17,000,000 Depositary Shares, Each Representing a 1/1000th Interest in a Share of 7.875% Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series F Underwriting Agreement

from 8-K 39 pages Wintrust Financial Corporation (An Illinois Corporation) 3,000,000 Shares of Common Stock Underwriting Agreement

from 8-K 36 pages Wintrust Financial Corporation (An Illinois Corporation) 10,000,000 Depositary Shares, Each Representing a 1/1000th Interest in a Share of 6.875% Fixed Rate Reset Non-Cumulative Perpetual Preferred Stock, Series E Underwriting Agreement

from 8-K 33 pages Wintrust Financial Corporation (An Illinois Corporation) $300,000,000 4.850% Subordinated Notes Due 2029 Underwriting Agreement

from 8-K 35 pages 3,000,000 Shares Wintrust Financial Corporation (An Illinois Corporation) Common Stock Underwriting Agreement

from 8-K 33 pages Wintrust Financial Corporation (An Illinois Corporation) Fixed-To-Floating Rate Non-Cumulative Perpetual Preferred Stock, Series D Underwriting Agreement

from 8-K 3 pages Wintrust Financial Corporation (An Illinois Corporation) $140,000,000 5.000% Subordinated Notes Due 2024 Underwriting Agreement

from 8-K 38 pages Wintrust Financial Corporation (An Illinois Corporation) 110,000 Shares 5.00% Non-Cumulative Perpetual Convertible Preferred Stock, Series C Purchase Agreement

from 8-K 36 pages 1,643,295 Warrants Wintrust Financial Corporation (An Illinois Corporation) Underwriting Agreement

from 8-K 40 pages Wintrust Financial Corporation (An Illinois Corporation) 4,000,000 Tangible Equity Units Purchase Agreement

from 8-K 36 pages Wintrust Financial Corporation (An Illinois Corporation) 3,205,128 Shares of Common Stock Purchase Agreement

from 8-K 34 pages Wintrust Financial Corporation (An Illinois Corporation) 5,800,000 Shares of Common Stock Purchase Agreement

from 425 10 pages This Letter Provides Highlights of Our Performance Through the Fourth Quarter of 2005. a More Detailed Analysis Will Be Available Shortly in Our 2005 Annual Report. We Have Also Attached a Copy of Our Selected Financial Highlights as Well as Our Consolidated Statements of Condition and Income for the Period Ended December 31, 2005. for Those of You That Would Like to View Our More Expanded Earnings Release and Additional Supplemental Financial Information, Please Visit Our Website at WWW.WINTRUST.com and View the Page Titled “Investor News” and Click on “Press Releases” or “Supplemental Financial Info.” Highlights for Fourth Quarter of 2005 for This Quarter, We Again Achieved Record Levels for Earnings, Assets, Deposit and Loans. Here Is a Summary of Our Financial Results and Accomplishments for the Period Ending December 31, 2005

from 8-K 10 pages This Letter Provides Highlights of Our Performance Through the Fourth Quarter of 2005. a More Detailed Analysis Will Be Available Shortly in Our 2005 Annual Report. We Have Also Attached a Copy of Our Selected Financial Highlights as Well as Our Consolidated Statements of Condition and Income for the Period Ended December 31, 2005. for Those of You That Would Like to View Our More Expanded Earnings Release and Additional Supplemental Financial Information, Please Visit Our Website at WWW.WINTRUST.com and View the Page Titled “Investor News” and Click on “Press Releases” or “Supplemental Financial Info.” Highlights for Fourth Quarter of 2005 for This Quarter, We Again Achieved Record Levels for Earnings, Assets, Deposit and Loans. Here Is a Summary of Our Financial Results and Accomplishments for the Period Ending December 31, 2005

from 8-K ~20 pages Forward Sale Agreement

from 8-K ~50 pages Underwriting Agreement

from S-3 ~50 pages Equity Underwriting Agreement

from S-3 ~50 pages Exhibit 1.1 - Form of Underwriting Agreement

from S-3 ~50 pages Underwriting agreement

from S-3 ~50 pages Form of Underwriting Agreement