| Year | Sport | Class | Champion | Runnerup | Score | Link |
| 2024 | Ice Hockey (Boys) | I | Notre Dame-West Haven | New Canaan | 4-1 | |
| Ice Hockey (Boys) | II | Cheshire | East Haven Coop | 6-3 | |
| Ice Hockey (Boys) | III | Conard | Bethel/Brookfield/Danbury/Immaculate | 4-1 | |
| 2023 | Ice Hockey (Boys) | I | Fairfield Prep | Notre Dame-West Haven | 3-0 | |
| Ice Hockey (Boys) | II | North Haven | Woodstock Academy | 2-1 | |
| Ice Hockey (Boys) | III | Masuk | Newington Coop | 6-3 | |
| 2022 | Ice Hockey (Boys) | I | Notre Dame-West Haven | Darien | 4-2 | |
| Ice Hockey (Boys) | II | Wethersfield | North Haven | 3-0 | |
| Ice Hockey (Boys) | III | Newington Coop | Conard | 3-1 | |
| 2020 | Ice Hockey (Boys) | I | | | | |
| Ice Hockey (Boys) | II | | | | |
| Ice Hockey (Boys) | III | | | | |
| 2019 | Ice Hockey (Boys) | I | Fairfield Prep | Notre Dame-West Haven | 5-2 | |
| Ice Hockey (Boys) | II | Branford | Glastonbury | 2-0 | |
| Ice Hockey (Boys) | III | Lyman Hall/H-K/Coginchaug | Sheehan | 6-2 | |
| 2018 | Ice Hockey (Boys) | I | Fairfield Prep | Greenwich | 4-2 | |
| Ice Hockey (Boys) | II | Farmington Valley | Guilford | 7-3 | |
| Ice Hockey (Boys) | III | Eastern CT Eagles | Tri-Town | 7-3 | |
| 2017 | Ice Hockey (Boys) | I | Ridgefield | Northwest Catholic | 6-2 | |
| Ice Hockey (Boys) | II | Guilford | Watertown-Pomperaug | 5-3 | |
| Ice Hockey (Boys) | III | Woodstock Academy | Hall-Southington | 7-3 | |
| 2016 | Ice Hockey (Boys) | I | Darien | Fairfield Prep | 4-2 | |
| Ice Hockey (Boys) | II | Fairfield Warde/Ludlowe | North Branford | 4-3 (OT) | |
| Ice Hockey (Boys) | III | Westhill-Stamford | SWS | 5-4 | |
| 2015 | Ice Hockey (Boys) | I | Darien | Greenwich | 1-0 | |
| Ice Hockey (Boys) | II | Suffield-Granby-Windsor Locks | North Branford | 4-1 | |
| Ice Hockey (Boys) | III | E.O. Smith-Tolland | Masuk | 5-2 | |
| 2014 | Ice Hockey (Boys) | I | Fairfield Prep | Darien | 2-1 (OT) | |
| Ice Hockey (Boys) | II | Daniel Hand | Amity | 5-4 | |
| Ice Hockey (Boys) | III | Newtown | E.O. Smith/Tolland | 2-1 (OT) | |
| 2013 | Ice Hockey (Boys) | I | Fairfield Prep | Notre Dame | 3-2 | |
| Ice Hockey (Boys) | II | Fairfield Warde/Ludlowe | East Catholic | 4-3 (OT) | |
| Ice Hockey (Boys) | III | Newington-Berlin-Manchester | Rockville-Coventry-Bolton-Lyman Memorial | 1-0 | |
| 2012 | Ice Hockey (Boys) | I | Notre Dame-West Haven | Glastonbury | 5-0 | |
| Ice Hockey (Boys) | II | Trumbull | Branford | 5-3 | |
| Ice Hockey (Boys) | III | Newington-Berlin | Northwest Catholic | 2-1 | |
| 2011 | Ice Hockey (Boys) | I | Fairfield Prep | St. Joseph | 5-0 | |
| Ice Hockey (Boys) | II | Cheshire | Guilford | 3-1 | |
| Ice Hockey (Boys) | III | Watertown-Pomperaug | Staples-Weston-Shelton | 4-0 | |
| 2010 | Ice Hockey (Boys) | I | Hamden | Fairfield Prep | 6-5 | |
| Ice Hockey (Boys) | II | Amity Regional | St. Joseph | 7-5 | |
| Ice Hockey (Boys) | III | Guilford | Brookfield-Bethel-Danbury | 7-3 | |
| 2009 | Ice Hockey (Boys) | I | Hamden | Glastonbury | 4-1 | |
| Ice Hockey (Boys) | II | Cheshire | Enfield | 3-2 | |
| Ice Hockey (Boys) | III | St. Joseph | Staples-Weston | 3-2 (2OT) | |
| 2008 | Ice Hockey (Boys) | I | Fairfield Prep | Notre Dame-Fairfield | 5-3 | |
| Ice Hockey (Boys) | II | Amity Regional | Fairfield Warde-Ludlowe | 5-1 | |
| Ice Hockey (Boys) | III | Rockville-Manchester | Bolton-Coventry-Lyman Memorial | 6-3 | |
| 2007 | Ice Hockey (Boys) | I | Fairfield Prep | Notre Dame-Fairfield | 3-2 (OT) | |
| Ice Hockey (Boys) | II | Immaculate | East Haven | 3-2 | |
| Ice Hockey (Boys) | III | Wethersfield | New Milford | 3-2 | |
| 2006 | Ice Hockey (Boys) | I | Notre Dame-Fairfield | Hamden | 4-2 | |
| Ice Hockey (Boys) | II | Daniel Hand | New Canaan | 1-0 | |
| Ice Hockey (Boys) | III | Cheshire | Newington | 2-0 | |
| 2005 | Ice Hockey (Boys) | I | Fairfield Prep | Notre Dame-West Haven | 4-1 | |
| Ice Hockey (Boys) | II | Farmington | Trumbull | 5-4 (2OT) | |
| 2004 | Ice Hockey (Boys) | I | Fairfield Prep | Notre Dame-West Haven | 3-1 | |
| Ice Hockey (Boys) | II | North Haven | Daniel Hand | 3-1 | |
| 2003 | Ice Hockey (Boys) | I | Simsbury | Hamden | 3-2 | |
| Ice Hockey (Boys) | II | Glastonbury | Shepaug Valley | 6-3 | |
| 2002 | Ice Hockey (Boys) | I | Notre Dame-West Haven | New Canaan | 4-1 | |
| Ice Hockey (Boys) | II | Ridgefield | Milford | 8-3 | |
| 2001 | Ice Hockey (Boys) | I | Fairfield Prep | Notre Dame-West Haven | 8-0 | |
| Ice Hockey (Boys) | II | Stamford | Westhill | 4-0 | |
| 2000 | Ice Hockey (Boys) | I | Fairfield Prep | Greenwich | 2-0 | |
| Ice Hockey (Boys) | II | Suffield | Immaculate | 1-0 | |
| 1999 | Ice Hockey (Boys) | I | Notre Dame-Fairfield | New Canaan | 3-2 (5OT) | |
| Ice Hockey (Boys) | II | Glastonbury | Cheshire | 4-3 (OT) | |
| 1998 | Ice Hockey (Boys) | I | Trinity Catholic | New Canaan | 3-1 | |
| Ice Hockey (Boys) | II | East Haven | Newington | 7-1 | |
| 1997 | Ice Hockey (Boys) | I | Notre Dame-West Haven | Simsbury | 6-3 | |
| Ice Hockey (Boys) | II | South Windsor | East Haven | 7-5 | |
| 1996 | Ice Hockey (Boys) | I | Fairfield Prep | New Canaan | 3-0 | |
| Ice Hockey (Boys) | II | Conard | East Haven | 6-2 | |
| 1995 | Ice Hockey (Boys) | I | Fairfield Prep | New Canaan | 6-1 | |
| Ice Hockey (Boys) | II | Rockville | East Haven | 4-3 | |
| 1994 | Ice Hockey (Boys) | I | West Haven | Notre Dame-West Haven | 7-4 | |
| Ice Hockey (Boys) | II | Guilford | East Windsor/Ellington/Somers (Coop) | 8-1 | |
| 1993 | Ice Hockey (Boys) | I | Notre Dame-West Haven | Trinity Catholic | 3-2 | |
| Ice Hockey (Boys) | II | Hall | Westhill | 4-3 | |
| 1992 | Ice Hockey (Boys) | I | Greenwich | Fairfield Prep | 3-2 | |
| Ice Hockey (Boys) | II | New Milford | Suffield | 4-3 | |
| 1991 | Ice Hockey (Boys) | I | Fairfield Prep | Hamden | 3-1 | |
| Ice Hockey (Boys) | II | Stamford Catholic | Cheshire | 3-1 | |
| 1990 | Ice Hockey (Boys) | I | West Haven | Greenwich | 4-0 | |
| Ice Hockey (Boys) | II | Enrico Fermi | Stamford Catholic | 7-6 | |
| 1989 | Ice Hockey (Boys) | I | Hamden | Notre Dame-West Haven | 1-0 | |
| Ice Hockey (Boys) | II | Notre Dame-Fairfield | Enrico Fermi | 7-3 | |
| 1988 | Ice Hockey (Boys) | I | West Haven | Notre Dame-West Haven | 2-1 | |
| Ice Hockey (Boys) | II | Branford | Shepaug Valley | 5-3 | |
| 1987 | Ice Hockey (Boys) | I | Notre Dame-West Haven | Darien | 4-3 (OT) | |
| Ice Hockey (Boys) | II | Enfield | Norwalk | 13-1 | |
| 1986 | Ice Hockey (Boys) | I | Hamden | Notre Dame-West Haven | 7-6 (OT) | |
| Ice Hockey (Boys) | II | Immaculate | Wethersfield | 8-7 (OT) | |
| 1985 | Ice Hockey (Boys) | I | Notre Dame-West Haven | Darien | 10-5 | |
| Ice Hockey (Boys) | II | Conard | Westhill | 5-4 (OT) | |
| 1984 | Ice Hockey (Boys) | I | West Haven | Darien | 4-3 | |
| Ice Hockey (Boys) | II | East Catholic | North Haven | 9-2 | |
| 1983 | Ice Hockey (Boys) | I | Enfield | Notre Dame-West Haven | 5-4 | |
| Ice Hockey (Boys) | II | Enrico Fermi | South Windsor | | |
| 1982 | Ice Hockey (Boys) | I | Notre Dame-West Haven | New Canaan | 4-2 | |
| Ice Hockey (Boys) | II | Enfield | East Haven | 5-4 | |
| 1981 | Ice Hockey (Boys) | I | Fairfield Prep | Hamden | 3-2 (OT) | |
| Ice Hockey (Boys) | II | Staples | Stamford Catholic | 3-2 | |
| 1980 | Ice Hockey (Boys) | I | Fairfield Prep | Amity | 3-1 | |
| Ice Hockey (Boys) | II | North Haven | Norwalk | 4-2 | |
| 1979 | Ice Hockey (Boys) | I | Fairfield Prep | Cheshire | 3-2 | |
| Ice Hockey (Boys) | II | Suffield | Westhill | 7-3 | |
| 1978 | Ice Hockey (Boys) | I | Cheshire | Fairfield Prep | 6-5 | |
| Ice Hockey (Boys) | II | Stamford | Notre Dame-West Haven | 5-0 | |
| 1977 | Ice Hockey (Boys) | I | West Haven | Hamden | 4-2 | |
| Ice Hockey (Boys) | II | Fairfield Prep | Cheshire | 4-3 | |
| 1976 | Ice Hockey (Boys) | I | Hamden | Amity | 4-3 | |
| Ice Hockey (Boys) | II | South Windsor | East Haven | 7-0 | |
| 1975 | Ice Hockey (Boys) | I | Hamden | West Haven | 6-1 | |
| 1974 | Ice Hockey (Boys) | I | Hamden | New Canaan | 4-2 | |
| 1973 | Ice Hockey (Boys) | I | Hamden | West Haven | 3-0 | |
| 1972 | Ice Hockey (Boys) | I | New Canaan | Hamden | 2-1 | |
| 1971 | Ice Hockey (Boys) | I | Hamden | Amity | 4-1 | |
| 1970 | Ice Hockey (Boys) | I | Hamden | New Canaan | 7-0 | |
| 1969 | Ice Hockey (Boys) | I | Darien | Hamden | 3-2 | |
| 1968 | Ice Hockey (Boys) | I | Hamden | Darien | | |
| 1967 | Ice Hockey (Boys) | I | Hamden | West Haven | 2-1 | |
| 1966 | Ice Hockey (Boys) | I | Hamden | West Haven | 4-1 | |
| 1965 | Ice Hockey (Boys) | I | Hamden | New Canaan | 4-1 | |
| 1964 | Ice Hockey (Boys) | I | West Haven | Amity | 5-3 | |
| 1952 | Ice Hockey (Boys) | I | Hamden | West Haven | 15-1 | |
| 1950 | Ice Hockey (Boys) | I | Hamden | West Haven | 5-2 | |
| 1949 | Ice Hockey (Boys) | I | West Haven | Hillhouse | 6-1 | |
| 1948 | Ice Hockey (Boys) | I | Hamden | West Haven | 3-2 | |