X0303 4 2009-05-08 0000814184 TCF FINANCIAL CORP TCB 0001204875 DAHL CRAIG R 200 LAKE STREET EAST WAYZATA MN 55391-1693 0 1 0 0 Executive Vice President Common Stock 2009-05-08 4 M 0 80000 A 189409 D Common Stock 2009-05-08 4 S 0 3500 16.04 D 165761 D Common Stock 2009-05-08 4 S 0 2000 16.05 D 163761 D Common Stock 2009-05-08 4 S 0 5800 16.06 D 157961 D Common Stock 2009-05-08 4 S 0 4800 16.07 D 153161 D Common Stock 2009-05-08 4 S 0 2700 16.08 D 150461 D Common Stock 2009-05-08 4 S 0 1600 16.09 D 148861 D Common Stock 2009-05-08 4 S 0 3100 16.10 D 145761 D Common Stock 2009-05-08 4 S 0 3952 16.11 D 141809 D Common Stock 2009-05-08 4 S 0 4100 16.12 D 137709 D Common Stock 2009-05-08 4 S 0 2500 16.13 D 135209 D Common Stock 2009-05-08 4 S 0 4200 16.14 D 131009 D Common Stock 2009-05-08 4 S 0 1500 16.15 D 129509 D Common Stock 2009-05-08 4 S 0 3500 16.16 D 126009 D Common Stock 2009-05-08 4 S 0 2800 16.17 D 123209 D Common Stock 2009-05-08 4 S 0 1000 16.18 D 122209 D Common Stock 2009-05-08 4 S 0 1000 16.19 D 121209 D Common Stock 2009-05-08 4 S 0 200 16.20 D 121009 D Common Stock 2009-05-08 4 S 0 1500 16.21 D 119509 D Common Stock 2009-05-08 4 S 0 100 16.22 D 119409 D Common Stock 2009-05-08 4 S 0 500 16.23 D 118909 D Common Stock 2009-05-08 4 S 0 4900 16.25 D 114009 D Common Stock 2009-05-08 4 S 0 1500 16.26 D 112509 D Common Stock 2009-05-08 4 S 0 800 16.28 D 111709 D Common Stock 2009-05-08 4 S 0 300 16.29 D 111409 D Common Stock 2009-05-08 4 S 0 2000 16.50 D 109409 D Common Stock 2810.875 I By KSOP as of 4/30/09 Common Stock 11847.559 I By SERP as of 4/30/09 Option (Right to Buy) 2009-05-08 4 M 0 20000 0 A 2000-01-01 2009-05-11 Common Stock 20000 0 D Option (right to buy) 2009-05-08 4 M 0 20000 0 A 2001-01-01 2009-05-11 Common Stock 20000 0 D Option (right to buy) 2009-05-08 4 M 0 20000 0 A 2002-01-01 2009-05-11 Common Stock 20000 0 D Option (right to buy) 2009-05-08 4 M 0 20000 0 A 2003-01-01 2009-05-11 Common Stock 20000 0 D Option (right to buy) 15.75 2018-01-21 Common Stock 225000 225000 D The filing of this statement shall not be construed as an admission that the undersigned is, for the purpose of Section 16 of the Securities and Exchange Act of 1934, the beneficial owner of any equity securities covered by this statement other than those owned directly by the undersigned. The shares noted are derivative securities based on the Reporting Person's benefits under a non-qualified plan. The option vests in 2 installments: 50% on January 1, 2011; the remaining 50% on January 1, 2012. The first nine transactions of Common Stock on 5/8/09, all transaction code S: (beginning balance of Directly-Owned shares 189,409) - 824 shares (D) at $15.95; 1,200 shares (D) at $15.96; 1,900 shares (D) at $15.97; 1,700 shares (D) at $15.98; 3,200 shares (D) at $15.99; 1,600 shares (D) at $16.00; 5,924 shares (D) at $16.01; 900 shares (D) at $16.02; 2,900 shares (D) at $16.03. (ending balance of Directly-Owned shares 169,261). Exercise price is $14.515625. (Filer software permits only 4 digits to right of decimal point.) Craig R. Dahl By POA Gregory J. Pulles 2009-05-12