2006 Football Playoffs Scoreboard |  |
| Class LL | |
| Championship Game | |
| #2 Greenwich 28, #1 Southington 7 | Final at Jess Dow Field, SCSU, New Haven |
| Semifinals | |
| #1 Southington 36, #4 Shelton 9 | Final at Southington |
| #2 Greenwich 34, #3 Fairfield Prep 0 | Final at Greenwich |
Class LL Details:
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| Class L | |
| Championship Game | |
| #4 Bunnell 28, #2 Staples 26 | Final at Ken Strong Stadium, West Haven |
| Semifinals | |
| #4 Bunnell 29, #1 Masuk 12 | Final at Benedict Field at Masuk |
| #2 Staples 24, #3 West Haven 7 | Final at Fairfield Warde |
Class L Details:
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| Class MM | |
| Championship Game | |
| #1 New Canaan 53, #2 Maloney 21 | Final at Arute Field, CCSU, New Britain |
| Semifinals | |
| #1 New Canaan 49, #4 Coventry/Windham Tech 14 | Final at New Canaan |
| #2 Maloney 40, #3 Berlin 14 | Final at Ceppa Field, Meriden |
Class MM Details:
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| Class M | |
| Championship Game | |
| #2 Hillhouse 28, #1 Windham 6 | Final at Arute Field, CCSU, New Britain |
| Semifinals | |
| #1 Windham 22, #4 Ledyard 0 | Final at Windham |
| #2 Hillhouse 40, #3 St Bernard/Norwich Tech 0 | Final at Frank 'Coach' Crisafi Field at East Haven |
Class M Details:
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| Class SS | |
| Championship Game | |
| #1 Holy Cross 40, #2 Stratford 0 | Final at Ken Strong Stadium, West Haven |
| Semifinals | |
| #1 Holy Cross 49, #4 Tolland 8 | Final at Municipal Stadium, Waterbury |
| #2 Stratford 48, #3 Griswold 6 | Final at Longbrook Park, Stratford |
Class SS Details:
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| Class S | |
| Championship Game | |
| #1 Ansonia 34, #2 Bloomfield 12 | Final at Jess Dow Field, SCSU, New Haven |
| Semifinals | |
| #1 Ansonia 47, #4 North Branford 14 | Final at Jarvis Field at the Nolan Complex, Ansonia |
| #2 Bloomfield 45, #3 Cromwell 14 | Final at Bloomfield |
Class S Details:
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