| Year | Sport | Class | Champion | Runnerup | Score | Link |
| 2023 | Tennis (Boys) | LL | Greenwich | Staples | 4-0 | |
| Tennis (Boys) | L | Wilton | New Canaan | 5-1 | |
| Tennis (Boys) | M | Avon | Weston | 7-0 | |
| Tennis (Boys) | S | Stonington | Nonnewaug | 6-1 | |
| Tennis (Boys) | Open | | | | |
| 2022 | Tennis (Boys) | LL | Staples | Greenwich | 4-1 | |
| Tennis (Boys) | L | Darien | New Canaan | 6-1 | |
| Tennis (Boys) | M | Avon | Joel Barlow | 6-1 | |
| Tennis (Boys) | S | Granby Memorial | Shepaug Valley | 7-0 | |
| Tennis (Boys) | Open | | | | |
| 2021 | Tennis (Boys) | LL | Staples | Westhill | 7-0 | |
| Tennis (Boys) | L | Darien | Wilton | 4-2 | |
| Tennis (Boys) | M | Avon | East Lyme | 6-1 | |
| Tennis (Boys) | S | Granby Memorial | Westbrook | 4-3 | |
| Tennis (Boys) | Open | | | | |
| 2019 | Tennis (Boys) | LL | Staples | Greenwich | | |
| Tennis (Boys) | L | Darien | New Canaan | | |
| Tennis (Boys) | M | Joel Barlow | Weston/Avon (tie) | | |
| Tennis (Boys) | S | Litchfield | Stonington/Old Lyme (tie) | | |
| Tennis (Boys) | Open | | | | |
| 2018 | Tennis (Boys) | LL | Staples | Greenwich | | |
| Tennis (Boys) | L | Daniel Hand | Darien | | |
| Tennis (Boys) | M | Weston | Avon | | |
| Tennis (Boys) | S | Litchfield | Old Lyme | | |
| Tennis (Boys) | Open | | | | |
| 2017 | Tennis (Boys) | LL | Staples | Greenwich | | |
| Tennis (Boys) | L | New Canaan | Daniel Hand | | |
| Tennis (Boys) | M | Weston | Avon | | |
| Tennis (Boys) | S | East Catholic | Nonnewaug | | |
| Tennis (Boys) | Open | | | | |
| 2016 | Tennis (Boys) | LL | Staples/Greenwich | | (Co-Champions) | |
| Tennis (Boys) | L | New Canaan | Daniel Hand | | |
| Tennis (Boys) | M | Weston | Branford | | |
| Tennis (Boys) | S | East Catholic | Old Saybrook | | |
| Tennis (Boys) | Open | | | | |
| 2015 | Tennis (Boys) | LL | Amity | Staples | | |
| Tennis (Boys) | L | New Canaan | Darien | | |
| Tennis (Boys) | M | Weston | Avon | | |
| Tennis (Boys) | S | East Catholic | Old Lyme/Old Saybrook | | |
| Tennis (Boys) | Open | | | | |
| 2014 | Tennis (Boys) | LL | Staples | Greenwich | | |
| Tennis (Boys) | L | Daniel Hand | Fairfield Warde | | |
| Tennis (Boys) | M | Guilford | Avon | | |
| Tennis (Boys) | S | Weston | East Catholic | | |
| Tennis (Boys) | Open | | | | |
| 2013 | Tennis (Boys) | LL | Greenwich | Staples | | |
| Tennis (Boys) | L | Daniel Hand/Fairfield Warde | (Co-Champions) | | |
| Tennis (Boys) | M | Avon | Guilford | | |
| Tennis (Boys) | S | East Catholic | Weston | | |
| Tennis (Boys) | Open | | | | |
| 2012 | Tennis (Boys) | LL | Greenwich | Staples | | |
| Tennis (Boys) | L | New Canaan | Fairfield Warde/Daniel Hand | | |
| Tennis (Boys) | M | Avon | Joel Barlow | | |
| Tennis (Boys) | S | Weston | East Catholic | | |
| Tennis (Boys) | Open | | | | |
| 2011 | Tennis (Boys) | LL | Staples | Greenwich | | |
| Tennis (Boys) | L | New Canaan | Daniel Hand | | |
| Tennis (Boys) | M | Avon | Stonington | | |
| Tennis (Boys) | S | Weston | East Catholic | | |
| Tennis (Boys) | Open | | | | |
| 2010 | Tennis (Boys) | LL | Greenwich | Fairfield Prep | | |
| Tennis (Boys) | L | New Canaan | Fairfield Warde | | |
| Tennis (Boys) | M | Guilford | Branford | | |
| Tennis (Boys) | S | Weston | Bolton/East Catholic | | |
| Tennis (Boys) | Open | | | | |
| 2009 | Tennis (Boys) | LL | Greenwich | Staples | | |
| Tennis (Boys) | L | New Canaan | Hall | | |
| Tennis (Boys) | M | Fairfield Warde/Darien | (Co-Champions) | | |
| Tennis (Boys) | S | Weston | East Catholic | | |
| Tennis (Boys) | Open | | | | |
| 2008 | Tennis (Boys) | LL | Greenwich | | | |
| Tennis (Boys) | L | Staples | Hall | | |
| Tennis (Boys) | M | Darien | Farfield Warde | | |
| Tennis (Boys) | S | Weston | Bolton | | |
| Tennis (Boys) | Open | | | | |
| 2007 | Tennis (Boys) | LL | Greenwich | Amity | | |
| Tennis (Boys) | L | Hall | Simsbury | | |
| Tennis (Boys) | M | Darien | Fairfield Warde | | |
| Tennis (Boys) | S | Weston | Bolton | | |
| Tennis (Boys) | Open | | | | |
| 2006 | Tennis (Boys) | LL | Greenwich | Amity | | |
| Tennis (Boys) | L | Staples | Simsbury | | |
| Tennis (Boys) | M | New Canaan | Darien | | |
| Tennis (Boys) | S | Weston | Tolland | | |
| Tennis (Boys) | Open | | | | |
| 2005 | Tennis (Boys) | LL | Greenwich | Amity | | |
| Tennis (Boys) | L | Staples | Hall | | |
| Tennis (Boys) | M | New Canaan | Joel Barlow | | |
| Tennis (Boys) | S | Weston | Haddam-Killingworth/Tolland | | |
| Tennis (Boys) | Open | | | | |
| 2004 | Tennis (Boys) | LL | Amity Regional | | | |
| Tennis (Boys) | L | Staples | | | |
| Tennis (Boys) | M | New Canaan | | | |
| Tennis (Boys) | S | Weston | | | |
| Tennis (Boys) | Open | | | | |
| 2003 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | Staples | | | |
| Tennis (Boys) | M | Joel Barlow | | | |
| Tennis (Boys) | S | Weston | | | |
| Tennis (Boys) | Open | | | | |
| 2002 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | Cheshire | | | |
| Tennis (Boys) | M | Joel Barlow | | | |
| Tennis (Boys) | S | Weston | | | |
| Tennis (Boys) | Open | | | | |
| 2001 | Tennis (Boys) | LL | Fairfield | | | |
| Tennis (Boys) | L | Staples | | | |
| Tennis (Boys) | M | New Canaan | | | |
| Tennis (Boys) | S | East Catholic | | | |
| Tennis (Boys) | Open | | | | |
| 2000 | Tennis (Boys) | LL | Greenwich | | | |
| Tennis (Boys) | L | Staples | | | |
| Tennis (Boys) | M | New Canaan | | | |
| Tennis (Boys) | S | Northwestern | | | |
| Tennis (Boys) | Open | | | | |
| 1999 | Tennis (Boys) | LL | Greenwich | | | |
| Tennis (Boys) | L | Staples | | | |
| Tennis (Boys) | M | New Canaan/Wethersfield | | | |
| Tennis (Boys) | S | Coginchaug Regional | | | |
| Tennis (Boys) | Open | | | | |
| 1998 | Tennis (Boys) | LL | Cheshire | | | |
| Tennis (Boys) | L | Simsbury | | | |
| Tennis (Boys) | MM | Staples | | | |
| Tennis (Boys) | M | Darien | | | |
| Tennis (Boys) | S | Canton | | | |
| 1997 | Tennis (Boys) | LL | Greenwich | | | |
| Tennis (Boys) | L | Cheshire | | | |
| Tennis (Boys) | MM | New Canaan/Wethersfield | (Co-Champions) | | |
| Tennis (Boys) | M | Joel Barlow | | | |
| Tennis (Boys) | S | Nonnewaug/Old Lyme | (Co-Champions) | | |
| 1996 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | Cheshire | | | |
| Tennis (Boys) | MM | New Canaan | | | |
| Tennis (Boys) | M | Darien | | | |
| Tennis (Boys) | S | Old Lyme | | | |
| 1995 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | Cheshire/Simsbury | (Co-Champions) | | |
| Tennis (Boys) | MM | New Canaan | | | |
| Tennis (Boys) | M | Barlow/Darien/Wilton | (Co-Champions) | | |
| Tennis (Boys) | S | Old Lyme | | | |
| 1994 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | New Canaan | | | |
| Tennis (Boys) | M | Brookfield/Darien | (Co-Champions) | | |
| Tennis (Boys) | S | Avon | | | |
| 1993 | Tennis (Boys) | LL | Greenwich | | | |
| Tennis (Boys) | L | Hall | | | |
| Tennis (Boys) | M | New Canaan | | | |
| Tennis (Boys) | S | Weston | | | |
| 1992 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | Hall/New Canaan | (Co-Champions) | | |
| Tennis (Boys) | M | Joel Barlow | | | |
| Tennis (Boys) | S | Old Lyme | | | |
| 1991 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | Staples | | | |
| Tennis (Boys) | M | Joel Barlow | | | |
| Tennis (Boys) | S | Weston | | | |
| 1990 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | Ridgefield | | | |
| Tennis (Boys) | M | Joel Barlow | | | |
| Tennis (Boys) | S | Old Saybrook | | | |
| 1989 | Tennis (Boys) | LL | Ridgefield/Fairfield Prep | (Co-Champions) | | |
| Tennis (Boys) | L | Darien/New Canaan | (Co-Champions) | | |
| Tennis (Boys) | M | Farmington/Maloney | | | |
| Tennis (Boys) | S | Weston | | | |
| 1988 | Tennis (Boys) | LL | Staples | | | |
| Tennis (Boys) | L | New Canaan | | | |
| Tennis (Boys) | M | Brookfield | | | |
| Tennis (Boys) | S | Weston | | | |
| 1987 | Tennis (Boys) | LL | Amity Regional | | | |
| Tennis (Boys) | L | New Canaan | | | |
| Tennis (Boys) | M | St. Joseph | | | |
| Tennis (Boys) | S | Shepaug Valley | | | |
| 1986 | Tennis (Boys) | LL | Fairfield Prep | | | |
| Tennis (Boys) | L | New Canaan | | | |
| Tennis (Boys) | M | St. Joseph | | | |
| Tennis (Boys) | S | Avon | | | |
| 1985 | Tennis (Boys) | LL | New Canaan/Stamford/Glastonbury/Greenwich | (Co-Champions) | | |
| Tennis (Boys) | L | Darien | | | |
| Tennis (Boys) | M | Weston | | | |
| Tennis (Boys) | S | Old Lyme | | | |
| 1984 | Tennis (Boys) | LL | Staples | | | |
| Tennis (Boys) | L | Wilton | | | |
| Tennis (Boys) | M | Weston | | | |
| Tennis (Boys) | S | Old Saybrook | | | |
| 1983 | Tennis (Boys) | LL | Staples | | | |
| Tennis (Boys) | L | Darien/Wilton | (Co-Champions) | | |
| Tennis (Boys) | M | Bethel/St. Paul Catholic | (Co-Champions) | | |
| Tennis (Boys) | S | Old Saybrook | | | |
| 1982 | Tennis (Boys) | LL | Staples | | | |
| Tennis (Boys) | L | Darien | | | |
| Tennis (Boys) | M | Bethel/St. Paul Catholic | (Co-Champions) | | |
| Tennis (Boys) | S | Old Saybrook | | | |
| 1981 | Tennis (Boys) | LL | Norwalk | | | |
| Tennis (Boys) | L | New Canaan | | | |
| Tennis (Boys) | M | Daniel Hand | | | |
| Tennis (Boys) | S | Weston | | | |
| Tennis (Boys) | Open | Glastonbury/Norwalk | (Co-Champions) | | |
| 1980 | Tennis (Boys) | LL | Norwalk | | | |
| Tennis (Boys) | L | New Canaan | | | |
| Tennis (Boys) | M | Daniel Hand | | | |
| Tennis (Boys) | S | Granby Memorial/Old Lyme/Valley Regional | (Co-Champions) | | |
| Tennis (Boys) | Open | Darien/Staples | (Co-Champions) | | |
| 1979 | Tennis (Boys) | LL | Hall | | | |
| Tennis (Boys) | L | New Canaan | | | |
| Tennis (Boys) | M | Weston | | | |
| Tennis (Boys) | S | Granby Memorial | | | |
| Tennis (Boys) | Open | Hall | | | |
| 1978 | Tennis (Boys) | LL | Westhill | | | |
| Tennis (Boys) | L | Darien | | | |
| Tennis (Boys) | M | Weston | | | |
| Tennis (Boys) | S | Valley Regional | | | |
| 1977 | Tennis (Boys) | LL | Westhill | | | |
| Tennis (Boys) | L | Darien | | | |
| Tennis (Boys) | M | Guilford | | | |
| Tennis (Boys) | S | Old Lyme | | | |
| Tennis (Boys) | Open | Darien | | | |
| 1976 | Tennis (Boys) | LL | New Canaan | | | |
| Tennis (Boys) | L | Darien | | | |
| Tennis (Boys) | M | East Catholic | | | |
| Tennis (Boys) | S | Weston | | | |
| Tennis (Boys) | Open | New Canaan/Weston | (Co-Champions) | | |
| 1975 | Tennis (Boys) | Open | New Canaan | | | |
| 1974 | Tennis (Boys) | Open | New Canaan | | | |
| 1973 | Tennis (Boys) | Open | Andrew Warde | | | |
| 1972 | Tennis (Boys) | Open | New Canaan | | | |
| 1971 | Tennis (Boys) | Open | Staples | | | |
| 1970 | Tennis (Boys) | Open | Roger Ludlowe | | | |
| 1969 | Tennis (Boys) | Open | New Canaan | | | |
| 1968 | Tennis (Boys) | Open | Wethersfield/New Canaan | (Co-Champions) | | |
| 1967 | Tennis (Boys) | Open | Wethersfield | | | |