| 2025 |
| Wed., Dec. 3 | @ Seymour | W 34-14 | 1st Round Playoffs | | Mon., Dec. 8 | @ Northwest Catholic | L 0-21 | 2nd Round Playoffs |
| 2024 |
| Thu., Nov. 28 | vs. Naugatuck | L 28-33 | 1st Round Playoffs | | Tue., Dec. 3 | vs. Valley Regional | W 48-22 | 2nd Round Playoffs | | Sun., Dec. 8 | vs. Woodland Regional | W 30-23 | Semi-finals Playoffs | | Sat., Dec. 14 | vs. Bloomfield | W 58-12 | Championship Game |
| 2023 |
| Fri., Nov. 3 | vs. Waterbury Career Academy | W 28-14 | 1st Round Playoffs | | Fri., Nov. 10 | vs. Cromwell/Portland | L 0-28 | 2nd Round Playoffs |
| 2022 |
| Tue., Nov. 29 | vs. North Branford | W 43-13 | 1st Round Playoffs | | Sun., Dec. 4 | vs. Woodland Regional | W 35-20 | Semi-finals Playoffs | | Sat., Dec. 10 | vs. Bloomfield | W 28-21 | Championship Game |
| 2021 |
| Tue., Nov. 30 | vs. Seymour | W 35-14 | 1st Round Playoffs | | Sun., Dec. 5 | @ Cromwell/Portland | L 7-46 | 2nd Round Playoffs |
| 2019 |
| Wed., Dec. 4 | vs. Plainfield | W 30-12 | 1st Round Playoffs | | Mon., Dec. 9 | vs. Sheehan | L 22-30 | 2nd Round Playoffs |
| 2018 |
| | Plainfield | W 42-0 | 1st Round Playoffs | | | Bloomfield | L 19-26 | Semi-finals Playoffs |
| 2017 |
| | Seymour | W 51-16 | 1st Round Playoffs | | | St. Joseph | L 36-42 | Semi-finals Playoffs | | | Stafford/Summers/E. Windsor | W 52-19 | Championship Game |
| 2016 |
| | Stafford/Summers/E. Windsor | W 48-0 | 1st Round Playoffs | | | Cromwell/Portland | W 49-28 | Semi-finals Playoffs | | | Rocky Hill | W 28-21 | Championship Game |
| 2015 |
| | Capital Prep | W 35-13 | 1st Round Playoffs | | | Trinity Catholic | W 31-22 | Semi-finals Playoffs | | | Bloomfield | L 20-31 | Championship Game |
| 2014 |
| | Windham | W 35-14 | Semi-finals Playoffs | | | Valley Regional | L 20-21 | Championship Game |
| 2013 |
| | Coginchaug Regional | W 49-21 | 1st Round Playoffs | | | Rocky Hill | W 49-27 | Semi-finals Playoffs | | | Woodland Regional | W 51-12 | Championship Game |
| 2012 |
| | Prince Tech | W 53-16 | 1st Round Playoffs | | | Hyde | W 41-13 | Semi-finals Playoffs | | | North Branford | W 59-26 | Championship Game |
| 2011 |
| | Bethel | W 35-6 | 1st Round Playoffs | | | Berlin | W 48-14 | Semi-finals Playoffs | | | Ledyard | W 38-0 | Championship Game |
| 2010 |
| | Hyde | W 47-26 | 1st Round Playoffs | | | Montville | W 46-15 | Semi-finals Playoffs | | | St. Josephs | L 28-49 | Championship Game |
| 2009 |
| | NW Catholic | L 0-24 | 1st Round Playoffs |
| 2008 |
| | North Branford | W 28-0 | 1st Round Playoffs | | | Cromwell | L 12-14 | Semi-finals Playoffs |
| 2007 |
| | NW Catholic | W 25-7 | Semi-finals Playoffs | | | New London | W 35-0 | Championship Game |
| 2006 |
| | North Branford | W 47-14 | Semi-finals Playoffs | | | Bloomfield | W 34-14 | Championship Game |
| 2004 |
| | Cromwell | L 19-27 | 1st Round Playoffs |
| 2003 |
| | Hyde | W 67-14 | Semi-finals Playoffs | | | Cromwell | W 55-0 | Championship Game |
| 2002 |
| | Immaculate | W 39-7 | Semi-finals Playoffs | | | ND Fairfield | W 44-14 | Championship Game |
| 2001 |
| | North Branford | L 20-21 | 1st Round Playoffs |
| 2000 |
| | Griswold | L 6-7 | 1st Round Playoffs |
| 1999 |
| | Tolland | W 35-22 | Semi-finals Playoffs | | | Bloomfield | L 0-56 | Championship Game |
| 1998 |
| | Putnam | W 45-21 | Semi-finals Playoffs | | | Bloomfield | L 7-40 | Championship Game |
| 1997 |
| | Darien | L 6-23 | 1st Round Playoffs |
| 1996 |
| | Darien | L 20-31 | 1st Round Playoffs |
| 1995 |
| | Sheehan | W 16-6 | Semi-finals Playoffs | | | Bloomfield | W 7-0 | Championship Game |
| 1994 |
| | Bloomfield | W 54-14 | Championship Game |
| 1992 |
| | New London | L 19-21 | Semi-finals Playoffs |
| 1991 |
| | New London | L 18-34 | Championship Game |
| 1989 |
| | Weston | W 44-0 | Championship Game |
| 1988 |
| | New London | W 20-15 | Championship Game |
| 1987 |
| | New London | W 28-27 | Championship Game |
| 1984 |
| | Putnan | W 56-6 | Championship Game |
| 1983 |
| | Stamford Catholic | W 32-0 | Championship Game |
| 1982 |
| | Derby | W 14-0 | Championship Game |
| 1981 |
| | Wilson | W 23-6 | Championship Game |
| 1980 |
| | Newington | L 14-24 | Championship Game |
| 1979 |
| | Seymour | W 28-14 | Championship Game |
| 1978 |
| | Amity | W 22-35 | Championship Game |
| 1977 |
| | Stamford Catholic | W 20-7 | Championship Game |
| 1976 |
| | Derby | W 6-0 | Championship Game |
|
| Ansonia Playoff Totals |
| Record |
55-22-0 2401-1366 |
| Home Record | 9-3 |
| Away Record | 1-2 |
|
