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2005—Another Year of Solid Growth for Wintrust Highlights • Earnings grew 31% • Diluted earnings per share grew 18% • Net revenue grew 28% • Net interest income grew 37% • Total assets grew 27% • Total deposits grew 32% • Total loans grew 20% • Total equity grew 32% • Book value per common share grew 20% • Dividends paid per share grew 20% • Return on average equity was 11.00% • Return on average assets stood at 0.88% • Successfully completed the acquisitions of - State Bank of The Lakes - First Northwest Bank • 13 bank charters • 23 total operating subsidiaries • Bank charter #14 de novo launch in early 2006 - Old Plank Trail Community Bank • Another acquisition scheduled to close in early 2006 - Hinsbrook Bank & Trust • Opened 12 net new banking facilities in Illinois and Wisconsin Contents 2 Selected Financial Trends 27 Acquisition Strategy 3 Selected Financial Highlights 28 Reports of Internal Control 4 To Our Fellow Shareholders 30 Consolidated Financial Statements 9 Overall Financial Performance 34 Notes to Consolidated Financial Statements 12 Wintrust Banking Locations 67 Report of Independent Auditors 13 Bank Brands We Market 68 Management’s Discussion and Analysis 14 Other Wintrust Locations 105 Leadership—Directors & Officers 15 Banking, Wealth Management and 114 Corporate Locations Other Companies Update 118 Corporate Information 21 Growth and Earnings Strategies Who Is Wintrust? For those of you new to our family, here is a brief description of who we are and what we do: Wintrust Financial Corporation is a financial holding company headquartered in Lake Forest, Illinois, with total assets of $8.2 billion as of December 31, 2005. At the end of 2005, Wintrust operated 13 community banks located in the greater Chicago and southern Wisconsin areas with 62 banking facilities. Of our 13 banking charters, eight were de novo banks started by Wintrust and five have been acquisitions. Our banks provide community-oriented personal and commercial banking services. Our wealth management companies provide trust, asset management and brokerage services to clients primarily located in the Midwest. We also originate and pur- chase residential mortgage loans, many of which are sold into the secondary market. And we are involved in specialty lending through operating subsidiaries or divisions of the Company’s banks. Our specialty lending niches include commercial insurance premium finance, accounts receivable financing and administrative services to the temporary staffing industry, condominium association lending, aircraft lending and indirect auto lending. We have always had a policy of presenting our goals, objectives and financial results in an up front manner to our shareholders. In this annual report, we are confirming our policy of reporting thoroughly the financial results, accounting policies and objectives of Wintrust Financial Corporation and our operating subsidiaries. We hope you enjoy the report. Selected Financial Trends Total Assets Earnings Per Share Net Income (end of year) (diluted) (000’s) $9,000M $3.00 8,000 $70,000 2.50 7,000 60,000 6,000 2.00 50,000 5,000 40,000 1.50 4,000 30,000 3,000 1.00 20,000 2,000 0.50 1,000 10,000 20012002 2003 2004 2005 2001 2002 2003 2004 2005 2001 2002 2003 2004 2005 Net Revenue Book Value Per Common Share Return On Average Equity $350M $30.00 15.0% 300 25.00 12.5 250 20.00 10.0 200 15.00 7.5 150 10.00 5.0 100 5.00 2.5 50 20012002 2003 2004 2005 2001 2002 2003 2004 2005 2001 2002 2003 2004 2005 Note: M=Million 2 WINTRUST FINANCIAL CORPORATION Selected Financial Highlights Years Ended December 31, 2005 2004 2003 2002 2001 (dollars in thousands, except per share data) Selected Financial Condition Data (at end of year): Total assets $ 8,177,042 $ 6,419,048 $ 4,747,398 $ 3,721,555 $ 2,705,422 Total loans 5,213,871 4,348,346 3,297,794 2,556,086 2,018,479 Total deposits 6,729,434 5,104,734 3,876,621 3,089,124 2,314,636 Notes payable 1,000 1,000 26,000 44,025 46,575 Federal Home Loan Bank advances 349,317 303,501 144,026 140,000 90,000 Subordinated notes 50,000 50,000 50,000 25,000 - Long-term debt — trust preferred securities 230,458 204,489 96,811 50,894 51,050 Total shareholders’ equity 627,911 473,912 349,837 227,002 141,278 Selected Statements of Operations Data: Net interest income $ 216,759 $ 157,824 $ 120,492 $ 98,128 $ 74,014 (1) Net revenue 310,316 243,276 193,084 158,800 102,812 Net income 67,016 51,334 38,118 27,875 18,439 Net income per common share - Basic 2.89 2.49 2.11 1.71 1.34 Net income per common share - Diluted 2.75 2.34 1.98 1.60 1.27 Cash dividends declared per common share 0.24 0.20 0.16 0.12 0.093 Selected Financial Ratios and Other Data: Performance Ratios: Net interest margin 3.16% 3.17% 3.20% 3.34% 3.49% Core net interest margin (2) 3.37 3.31 3.32 3.51 3.73 Non-interest income to average assets 1.23 1.57 1.76 1.89 1.24 Non-interest expense to average assets 2.62 2.86 2.98 3.30 2.83 Net overhead ratio (3) 1.39 1.30 1.22 1.41 1.59 Efficiency ratio (4) 63.97 64.45 63.52 66.41 63.66 Return on average assets 0.88 0.94 0.93 0.87 0.79 Return on average equity 11.00 13.12 14.36 14.76 15.24 Average total assets $ 7,587,602 $ 5,451,527 $ 4,116,618 $ 3,212,467 $ 2,328,032 Average total shareholders’ equity 609,167 391,335 265,495 188,849 120,995 Ending loan-to-deposit ratio 77.5% 85.2% 85.1% 82.7% 87.2% Average loans to average deposits ratio 83.4 87.7 86.4 88.5 87.4 Average interest earning assets to average interest bearing liabilities 108.83 109.89 109.68 109.86 109.35 Asset Quality Ratios: Non-performing loans to total loans 0.50% 0.43% 0.72% 0.49% 0.64% Non-performing assets to total assets 0.34 0.29 0.51 0.34 0.48 Allowance for credit losses(5) to: Total loans 0.78 0.79 0.77 0.72 0.68 Non-performing loans 155.69 184.13 107.59 146.63 105.63 Common Share Data at end of year: Market price per common share $ 54.90 $ 56.96 $ 45.10 $ 31.32 $ 20.38 Book value per common share $ 26.23 $ 21.81 $ 17.43 $ 13.19 $ 9.72 Common shares outstanding 23,940,744 21,728,548 20,066,265 17,216,270 14,531,665 Other Data at end of year: Number of: Bank subsidiaries 13 12977 Non-bank subsidiaries 10 10773 Banking offices 62 50 36 31 29 (1) Net revenue is net interest income plus non-interest income. (2) The core net interest margin excludes the effect of the net interest expense associated with the Company’s Long-Term Debt — Trust Preferred Securities. (3) The net overhead ratio is calculated by netting total non-interest expense and total non-interest income and dividing by that period’s total average assets. A lower ratio indicates a higher degree of efficiency. (4) The efficiency ratio is calculated by dividing total non-interest expense by tax-equivalent net revenues (less securities gains or losses). A lower ratio indicates more efficient revenue generation. (5) The allowance for credit losses includes both the allowance for loan losses and the allowance for lending-related commitments. 2005 ANNUAL REPORT 3 To Our Fellow Shareholders, Welcome to Wintrust Financial Corporation’s tenth Wintrust completed two bank acquisitions in 2005—Anti- annual report. And thank you for being a shareholder. och Holding Company (January) and First Northwest Bancorp, Inc. (March). We welcome their employees, We Have Come a Long Way customers and shareholders to the Wintrust family. When our first bank opened in 1991, we strongly Antioch Holding Company was the parent company of believed in a simple, but powerful concept—introducing State Bank of The Lakes (SBOTL). SBOTL, which is and operating a network of locally run community banks over 100 years old, has locations in Antioch, Linden- that really do provide better customer service than the hurst, Grayslake, Spring Grove and McHenry, Illinois that big bank alternatives. Little did we know that this would significantly expand Wintrust’s community banking net- quickly grow into a family of 23 companies with over work into northern Lake County and McHenry County. 1,600 full-time equivalent employees serving over 250,000 client relationships. First Northwest Bancorp was the parent company of First Northwest Bank (opened in 1995 as a de novo bank) with $8 Billion at Such a Young Age two locations in Arlington Heights, Illinois. In 2005, First In 2005, Wintrust again generated record growth in net Northwest Bank merged with our Village Bank and Trust income (up $15.7 million or 31%), net revenue (up $67.0 Company-Arlington Heights to form the new Village Bank million or 28%), assets (up $1.8 billion or 27%), deposits & Trust. This gives us four banking locations and a signif- (up $1.6 billion or 32%), and loans (up $866 million or icant market share in this important banking market. 20%). And once again, Wintrust is one of the fastest In December, Wintrust announced an agreement to growing financial services groups in the U.S.

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