| Year | Sport | Class | Champion | Runnerup | Score | Link |
| 2023 | Soccer (Boys) | LL | Hall | Stamford | 1-0 | |
| Soccer (Boys) | L | East Lyme | Notre Dame-West Haven | 3-2 | |
| Soccer (Boys) | M | Lewis Mills | Stonington | 5-2 | |
| Soccer (Boys) | S | Old Saybrook | Shepaug Valley | 4-1 | |
| 2022 | Soccer (Boys) | LL | Greenwich | Hall | 3-2 (PK4-3) | |
| Soccer (Boys) | L | Cheshire | Xavier | 3-1 | |
| Soccer (Boys) | M | Ellington | Weston | 2-1 (2OT) | |
| Soccer (Boys) | S | Old Saybrook | East Hampton | 2-0 | |
| 2021 | Soccer (Boys) | LL | Farmington | Cheshire | 3-2 | |
| Soccer (Boys) | L | Wethersfield | Fitch | 4-1 | |
| Soccer (Boys) | M | Stonington | Ellington | 3-1 | |
| Soccer (Boys) | S | Old Saybrook | Canton | 4-1 (OT) | |
| 2019 | Soccer (Boys) | LL | Hall | Greenwich | 3-1 | |
| Soccer (Boys) | L | Daniel Hand | Wilton | 4-3 (2OT) | |
| Soccer (Boys) | M | Stonington | Ellington | 1-0 | |
| Soccer (Boys) | S | Old Saybrook | Holy Cross | 3-1 (2OT) | |
| 2018 | Soccer (Boys) | LL | Glastonbury | Hall | 1-0 | |
| Soccer (Boys) | L | Daniel Hand | Maloney | 1-0 | |
| Soccer (Boys) | M | Plainville | Ellington | 1-0 | |
| Soccer (Boys) | S | Old Saybrook | Morgan | 2-1 | |
| 2017 | Soccer (Boys) | LL | Glastonbury | Naugatuck | 1-0 | |
| Soccer (Boys) | L | Daniel Hand | Masuk | 2-1 | |
| Soccer (Boys) | M | Lewis Mills | Suffield | 3-2 | |
| Soccer (Boys) | S | Morgan | Somers | 4-0 | |
| 2016 | Soccer (Boys) | LL | Farmington | Shelton | 3-0 | |
| Soccer (Boys) | L | Daniel Hand | Joel Barlow | 1-0 (2OT) | |
| Soccer (Boys) | M | Brookfield | Ellington | 1-0 | |
| Soccer (Boys) | S | Coventry | Old Saybrook | 2-0 | |
| 2015 | Soccer (Boys) | LL | Glastonbury | Darien | 4-0 | |
| Soccer (Boys) | L | Avon | Wethersfield | 3-1 (2OT) | |
| Soccer (Boys) | M | Tolland | Bacon Academy | 2-1 | |
| Soccer (Boys) | S | Somers | Coventry | 3-2 (2OT) | |
| 2014 | Soccer (Boys) | LL | Glastonbury | Farmington | 2-1 (2OT) | |
| Soccer (Boys) | L | Avon/Branford | | 1-1 (Co-Champions) | |
| Soccer (Boys) | M | Ellington | Tolland | 1-0 | |
| Soccer (Boys) | S | East Hampton/Somers | | 0-0 (Co-Champions) | |
| 2013 | Soccer (Boys) | LL | Ridgefield/Glastonbury | | (OT, Co-Champions) | |
| Soccer (Boys) | L | Farmington | Joel Barlow | 4-0 | |
| Soccer (Boys) | M | Suffield | Ellington | 2-0 | |
| Soccer (Boys) | S | Cromwell | Bolton | 3-0 | |
| 2012 | Soccer (Boys) | LL | Norwalk | Fairfield Prep | 2-0 | |
| Soccer (Boys) | L | Farmington | Avon | 5-0 | |
| Soccer (Boys) | M | Suffield | Bacon Academy | 3-2 (2OT) | |
| Soccer (Boys) | S | Bloomfield | Somers | 3-2 | |
| 2011 | Soccer (Boys) | LL | Pomperaug | Trumbull | 2-1 | |
| Soccer (Boys) | L | Bunnell | Avon | 3-0 | |
| Soccer (Boys) | M | Suffield | Granby Memorial | 2-0 | |
| Soccer (Boys) | S | Somers | Litchfield | 7-1 | |
| 2010 | Soccer (Boys) | LL | Farmington | Staples | 2-1 | |
| Soccer (Boys) | L | New Canaan | Bunnell | 2-0 | |
| Soccer (Boys) | M | Montville/Bethel | (Co-Champions) | 1-1 (OT) | |
| Soccer (Boys) | S | Somers | Valley Regional | 3-1 | |
| 2009 | Soccer (Boys) | LL | Staples | New Milford | 4-0 | |
| Soccer (Boys) | L | Brookfield | New Canaan | 3-2 | |
| Soccer (Boys) | M | Tolland | Granby Memorial | 2-1 | |
| Soccer (Boys) | S | Cromwell | Lyman Memorial | 1-0 | |
| 2008 | Soccer (Boys) | LL | Farmington | Glastonbury | 2-1 | |
| Soccer (Boys) | L | Wethersfield | East Lyme | 3-2 | |
| Soccer (Boys) | M | Ellington | Granby Memorial | 5-1 | |
| Soccer (Boys) | S | Old Lyme/Somers | (Co-Champions) | 2-2 (2OT) | |
| 2007 | Soccer (Boys) | LL | Ridgefield | Glastonbury | 1-0 | |
| Soccer (Boys) | L | Brookfield/Joel Barlow | (Co-Champions) | 1-1 (2OT) | |
| Soccer (Boys) | M | Ellington | East Catholic | 3-2 | |
| Soccer (Boys) | S | Kolbe Cathedral | Cromwell | 2-1 | |
| 2006 | Soccer (Boys) | LL | Simsbury | Staples | 2-1 (OT) | |
| Soccer (Boys) | L | New Canaan | Fermi | 4-3 (2OT) | |
| Soccer (Boys) | M | Suffield | Joel Barlow | 1-0 | |
| Soccer (Boys) | S | East Catholic | Cromwell | 3-0 | |
| 2005 | Soccer (Boys) | LL | Glastonbury | Farmington | 2-1 | |
| Soccer (Boys) | L | New Canaan | Seymour | 3-0 | |
| Soccer (Boys) | M | East Catholic/Weston | (Co-Champions) | 1-1 (2OT) | |
| Soccer (Boys) | S | Granby Memorial | East Hampton | 1-0 | |
| 2004 | Soccer (Boys) | LL | Newtown | Norwalk | 3-1 | |
| Soccer (Boys) | L | Wethersfield | Wilton | 2-0 | |
| Soccer (Boys) | M | North Branford | Avon | 2-0 | |
| Soccer (Boys) | S | Somers | Northwest Catholic | 4-3 (2OT) | |
| 2003 | Soccer (Boys) | LL | Simsbury/Glastonbury | (Co-Champions) | 0-0 | |
| Soccer (Boys) | L | Farmington | East Lyme | 1-0 | |
| Soccer (Boys) | M | North Branford | Ellington | 2-0 | |
| Soccer (Boys) | S | Canton | Lyman Memorial | 2-1 | |
| 2002 | Soccer (Boys) | LL | Naugatuck | Newtown | 3-2 (2 OT) | |
| Soccer (Boys) | L | Wethersfield/East Lyme | (Co-Champions) | 1-1 (2 OT) | |
| Soccer (Boys) | M | Nonnewaug | North Branford | 2-1 | |
| Soccer (Boys) | S | Northwest Catholic/Lyman Memorial | (Co-Champions) | 1-1 (2 OT) | |
| 2001 | Soccer (Boys) | LL | Naugatuck | Westhill | 3-2 | |
| Soccer (Boys) | L | Ledyard | Farmington | 2-0 | |
| Soccer (Boys) | M | Joel Barlow | North Branford | 2-1 | |
| Soccer (Boys) | S | Granby Memorial/Wheeler | (Co-Champions) | 1-1 (2 OT) | |
| 2000 | Soccer (Boys) | LL | Guilford | Fairfield | 3-2 | |
| Soccer (Boys) | L | Wethersfield | Newington | 2-1 (OT) | |
| Soccer (Boys) | M | Avon | Lewis Mills | 3-2 | |
| Soccer (Boys) | S | Granby Memorial | Valley Regional | 2-0 | |
| 1999 | Soccer (Boys) | LL | Glastonbury | Guilford | 1-0 (OT) | |
| Soccer (Boys) | L | Wethersfield | Daniel Hand | 2-0 | |
| Soccer (Boys) | M | Rocky Hill | Avon | 2-1 | |
| Soccer (Boys) | S | Wheeler | Valley Regional | 1-0 | |
| 1998 | Soccer (Boys) | LL | E.O. Smith/Danbury | (Co-Champions) | 2-2 (2 OT) | |
| Soccer (Boys) | L | Wilton | Newtown | 2-0 | |
| Soccer (Boys) | M | Joel Barlow | Suffield | 1-0 (2 OT) | |
| Soccer (Boys) | S | Cromwell | Old Saybrook | 2-0 | |
| 1997 | Soccer (Boys) | LL | Danbury | Guilford | 1-0 | |
| Soccer (Boys) | L | Daniel Hand/Woodstock Academy | (Co-Champions) | 0-0 (2 OT) | |
| Soccer (Boys) | M | Lewis Mills | North Branford | 1-0 | |
| Soccer (Boys) | S | Valley Regional/Immaculate | (Co-Champions) | 1-1 | |
| 1996 | Soccer (Boys) | LL | Guilford | Staples | 1-0 (OT) | |
| Soccer (Boys) | L | Bethel | Lyman Hall | 2-0 | |
| Soccer (Boys) | M | Farmington | Joel Barlow | 3-1 | |
| Soccer (Boys) | S | Immaculate | Tourtellotte | 4-1 | |
| 1995 | Soccer (Boys) | LL | Xavier | Simsbury | 2-1 | |
| Soccer (Boys) | L | Daniel Hand | Farmington | 5-1 | |
| Soccer (Boys) | M | RHAM | Avon | 2-1 | |
| Soccer (Boys) | S | Canton | Kolbe Cathedral | 4-1 | |
| 1994 | Soccer (Boys) | LL | E.O. Smith | Danbury | 1-0 | |
| Soccer (Boys) | L | Bethel | Farmington | 3-0 | |
| Soccer (Boys) | M | Rocky Hill | Stonington | 2-1 | |
| Soccer (Boys) | S | Windsor Locks | Old Saybrook | 2-1 | |
| 1993 | Soccer (Boys) | LL | Staples | E.O. Smith | 3-1 | |
| Soccer (Boys) | L | Daniel Hand | Newtown | 4-1 | |
| Soccer (Boys) | M | Stonington/RHAM | (Co-Champions) | 3-3 | |
| Soccer (Boys) | S | Granby Memorial/Bolton | (Co-Champions) | 1-1 | |
| 1992 | Soccer (Boys) | LL | Simsbury | Staples | 3-0 | |
| Soccer (Boys) | L | Farmington | Wilton | 1-0 (OT) | |
| Soccer (Boys) | M | Joel Barlow | Rocky Hill | 2-1 | |
| Soccer (Boys) | S | Cromwell | Old Lyme | 2-1 | |
| 1991 | Soccer (Boys) | LL | E.O. Smith | Danbury | 1-0 | |
| Soccer (Boys) | L | Wethersfield | Foran | 2-0 | |
| Soccer (Boys) | M | Joel Barlow/Suffield | (Co-Champions) | 0-0 | |
| Soccer (Boys) | S | Granby Memorial | Nonnewaug | 3-0 | |
| 1990 | Soccer (Boys) | LL | Danbury | Hartford Public | 2-1 | |
| Soccer (Boys) | L | Newtown | Guilford | 1-0 | |
| Soccer (Boys) | M | Joel Barlow | Avon | 2-1 | |
| Soccer (Boys) | S | Windsor Locks | Ellington | 1-0 | |
| 1989 | Soccer (Boys) | LL | Glastonbury | Danbury | 1-0 | |
| Soccer (Boys) | L | Guilford | East Lyme | 5-0 | |
| Soccer (Boys) | M | Avon | Joel Barlow | 3-2 | |
| Soccer (Boys) | S | Granby Memorial | Ellington | 7-0 | |
| 1988 | Soccer (Boys) | LL | Cheshire | Manchester | 2-1 | |
| Soccer (Boys) | L | Wilton | Brien McMahon | 2-1 | |
| Soccer (Boys) | M | Avon | Stonington | 2-1 | |
| Soccer (Boys) | S | Rocky Hill/Wheeler | (Co-Champions) | 1-1 (2 OT) | |
| 1987 | Soccer (Boys) | LL | E.O. Smith | Danbury | 1-0 | |
| Soccer (Boys) | L | Bethel | Enfield | 3-0 | |
| Soccer (Boys) | M | Avon | Waterford | 2-0 | |
| Soccer (Boys) | S | Granby Memorial | Canton | 1-0 | |
| 1986 | Soccer (Boys) | LL | Windham | Ridgefield | 1-0 | |
| Soccer (Boys) | L | Guilford | Wilton | 3-1 | |
| Soccer (Boys) | M | Farmington | Avon | 3-1 | |
| Soccer (Boys) | S | Granby Memorial | Central Catholic | 1-0 | |
| 1985 | Soccer (Boys) | LL | E.O. Smith | Holy Cross | 2-1 | |
| Soccer (Boys) | L | Guilford | Newtown | 4-0 | |
| Soccer (Boys) | M | Avon | Brookfield | 3-1 | |
| Soccer (Boys) | S | Granby Memorial | Marianapolis Prep | 4-1 | |
| 1984 | Soccer (Boys) | LL | Ridgefield | Glastonbury | 3-2 | |
| Soccer (Boys) | L | St. Paul Catholic/Wethersfield | (Co-Champions) | 1-1 | |
| Soccer (Boys) | M | Avon | Joel Barlow | 2-0 | |
| Soccer (Boys) | S | Granby Memorial | Old Lyme | 3-1 | |
| 1983 | Soccer (Boys) | LL | Ridgefield | Manchester | 3-0 | |
| Soccer (Boys) | L | Guilford | Hall | 1-0 | |
| Soccer (Boys) | M | Joel Barlow | Lyman Hall | 4-0 | |
| Soccer (Boys) | S | Old Saybrook | Granby Memorial | 1-0 | |
| 1982 | Soccer (Boys) | LL | Staples | Ridgefield | 1-0 | |
| Soccer (Boys) | L | Bethel/Wethersfield | (Co-Champions) | 1-1 | |
| Soccer (Boys) | M | Farmington | Waterford | 2-1 | |
| Soccer (Boys) | S | Old Saybrook | Coventry | 2-1 | |
| 1981 | Soccer (Boys) | LL | Simsbury/Staples | (Co-Champions) | 1-1 | |
| Soccer (Boys) | L | Bethel/Bullard Havens Tech | (Co-Champions) | 0-0 | |
| Soccer (Boys) | M | Suffield | Valley Regional | 1-0 | |
| Soccer (Boys) | S | Canton | Rocky Hill | 3-0 | |
| 1980 | Soccer (Boys) | LL | Hall | E.O. Smith | 3-2 | |
| Soccer (Boys) | L | Guilford | South Windsor | 6-1 | |
| Soccer (Boys) | M | St. Paul Catholic | Suffield | 1-0 | |
| Soccer (Boys) | S | Rocky Hill | Wamogo Regional | 3-0 | |
| 1979 | Soccer (Boys) | LL | Manchester | Glastonbury | 3-0 | |
| Soccer (Boys) | L | South Windsor | Guilford | 3-2 | |
| Soccer (Boys) | M | Farmington | Suffield | 2-1 | |
| Soccer (Boys) | S | Old Saybrook/Rocky Hill | (Co-Champions) | | |
| 1978 | Soccer (Boys) | LL | Staples | Greenwich | 3-2 | |
| Soccer (Boys) | L | Guilford | Windsor Locks | 4-1 | |
| Soccer (Boys) | M | Suffield | RHAM | 1-0 | |
| Soccer (Boys) | S | Granby Memorial | Woodstock Academy | 1-0 | |
| 1977 | Soccer (Boys) | LL | Hartford Public | Danbury | 4-3 | |
| Soccer (Boys) | L | Guilford | South Windsor | 4-0 | |
| Soccer (Boys) | M | RHAM/Valley Regional | (Co-Champions) | | |
| Soccer (Boys) | S | Old Lyme | Canton | 4-1 | |
| 1976 | Soccer (Boys) | LL | E.O. Smith | Brien McMahon | 3-0 | |
| Soccer (Boys) | L | Guilford | Windsor Locks | 1-0 | |
| Soccer (Boys) | M | Avon | Middletown | 3-0 | |
| Soccer (Boys) | S | Rocky Hill | Old Lyme | 2-0 | |
| 1975 | Soccer (Boys) | LL | Wethersfield | Manchester | 1-0 | |
| Soccer (Boys) | L | Bulkeley | Bullard Havens Tech | 2-0 | |
| Soccer (Boys) | M | E.O. Smith | Valley Regional | 2-1 | |
| Soccer (Boys) | S | Rocky Hill | Litchfield | 1-0 | |
| 1974 | Soccer (Boys) | L | Brien McMahon | Bulkeley | 2-0 | |
| Soccer (Boys) | M | Farmington | Guilford | 1-0 | |
| Soccer (Boys) | S | Old Lyme | Rocky Hill | 1-0 | |
| 1973 | Soccer (Boys) | L | Staples | Manchester | 1-0 | |
| Soccer (Boys) | M | Guilford | Farmington | 1-0 | |
| Soccer (Boys) | S | Canton | Old Lyme | 3-1 | |
| 1972 | Soccer (Boys) | L | Staples | Conard | 1-0 | |
| Soccer (Boys) | M | E.O. Smith | Windsor Locks | 1-0 | |
| Soccer (Boys) | S | Ellington | Coventry | 2-0 | |
| 1971 | Soccer (Boys) | L | Staples | Conard | 1-0 | |
| Soccer (Boys) | M | Windsor Locks | E.O. Smith | 2-1 | |
| Soccer (Boys) | S | Ellington | Rocky Hill | 2-1 | |
| 1970 | Soccer (Boys) | L | Conard/Staples | (Co-Champions) | | |
| Soccer (Boys) | M | Windsor Locks | St. Paul | 8-0 | |
| Soccer (Boys) | S | East Granby | Weston | 1-0 | |
| 1969 | Soccer (Boys) | L | Staples | Hartford Public | 2-0 | |
| Soccer (Boys) | M | Guilford | St. Paul | 4-0 | |
| Soccer (Boys) | S | Old Lyme | East Granby | 3-1 | |
| 1968 | Soccer (Boys) | L | Wethersfield | Staples | 1-0 | |
| Soccer (Boys) | M | E.O. Smith | Vinal Tech | 2-1 | |
| Soccer (Boys) | S | RHAM | East Hampton | 2-1 | |
| 1967 | Soccer (Boys) | L | Staples | Brien McMahon | 3-0 | |
| Soccer (Boys) | M | E.O. Smith | Simsbury | 4-0 | |
| Soccer (Boys) | S | Rocky Hill | Litchfield | 2-0 | |
| 1966 | Soccer (Boys) | L | Norwalk | Wethersfield | 1-0 | |
| Soccer (Boys) | M | Abbott Tech | Valley Regional | 1-0 | |
| Soccer (Boys) | S | Old Lyme | Hale Ray | 2-1 | |
| 1965 | Soccer (Boys) | L | Brien McMahon | Manchester | 1-0 | |
| Soccer (Boys) | M | E.O. Smith | Rocky Hill | 2-1 | |
| Soccer (Boys) | S | Washington | East Hampton | 1-0 | |
| 1964 | Soccer (Boys) | L | Hall | Brien McMahon | 2-1 | |
| Soccer (Boys) | M | Windsor Locks | Lewis Mills | 3-0 | |
| Soccer (Boys) | S | Morgan | Rocky Hill | 1-0 | |
| 1963 | Soccer (Boys) | L | Staples/Hall | (Co-Champions) | | |
| Soccer (Boys) | M | Windsor Locks | Winsted | 1-0 | |
| Soccer (Boys) | S | Litchfield | Rocky Hill | 1-0 | |
| 1962 | Soccer (Boys) | L | Manchester | Staples | 3-0 | |
| Soccer (Boys) | M | E.O. Smith | New Canaan | 2-1 | |
| Soccer (Boys) | S | Hale Ray | Thomaston | 3-0 | |
| 1961 | Soccer (Boys) | L-M | Greenwich | Manchester | 2-1 | |
| Soccer (Boys) | S | Hale Ray | Newtown | 5-1 | |
| 1960 | Soccer (Boys) | L-M | Glastonbury/Hall | (Co-Champions) | 1-1 | |
| Soccer (Boys) | S | Suffield | Hale Ray | 1-0 | |
| 1959 | Soccer (Boys) | L-M | Glastonbury | Hall | 1-0 | |
| Soccer (Boys) | S | Hale Ray | East Hampton | 4-3 | |
| 1958 | Soccer (Boys) | L-M | Manchester | Greenwich | 1-0 | |
| Soccer (Boys) | S | Hale Ray/Suffield | (Co-Champions) | 2-2 | |
| 1957 | Soccer (Boys) | L-M | Wethersfield | Newington | 3-0 | |
| Soccer (Boys) | S | Hale Ray | Ellsworth | 4-1 | |
| 1956 | Soccer (Boys) | L-M | Manchester | Norwalk | 2-0 | |
| Soccer (Boys) | S | Old Saybrook | Watertown | 1-0 | |
| 1955 | Soccer (Boys) | L-M | Wethersfield/Hall | (Co-Champions) | | |
| Soccer (Boys) | S | Valley Regional | Hale Ray | 1-0 | |
| 1954 | Soccer (Boys) | L-M | Wethersfield | Manchester | 4-1 | |
| Soccer (Boys) | S | Hale Ray | Portland | 3-2 | |
| 1953 | Soccer (Boys) | L-M | Hall | Manchester | 3-1 | |
| Soccer (Boys) | S | Hale Ray | Watertown | 2-0 | |
| 1952 | Soccer (Boys) | L-M | Hall | Wethersfield | 2-0 | |
| Soccer (Boys) | S | Hale Ray | Watertown | 2-0 | |
| 1951 | Soccer (Boys) | L-M | Hall | Manchester | 1-0 | |
| Soccer (Boys) | S | Ellsworth | Glastonbury | 3-0 | |
| 1950 | Soccer (Boys) | L-M | Newington | Wethersfield | 2-1 | |
| Soccer (Boys) | S | Bloomfield | Ellsworth | 1-1 (CK) | |
| 1949 | Soccer (Boys) | L-M | Wethersfield | Stamford | 2-0 | |
| Soccer (Boys) | S | Ellsworth | Bloomfield | 2-2 (CK) | |
| 1948 | Soccer (Boys) | L-M | Wethersfield | Hale Ray | 2-1 | |