| 2025 | Vernon Orioles | M&T Bank | McKenna Field |
| 2024 | M&T Bank | Vernon Orioles | Palmer Field |
| 2023 | Rainbow Graphics; Vernon Orioles | East Hartford Jets | Palmer Field |
| 2022 | Record-Journal Expos; East Hartford Jets | East Hartford Jets | Palmer Field |
| 2021 | Vernon Orioles | East Hartford Jets | Palmer Field |
| 2020 | South Windsor Phillies | East Hartford Jets | McKenna Field |
| 2019 | Record-Journal Expos | Vernon Orioles | Palmer Field |
| 2018 | Vernon Orioles | Vernon Orioles | Trinity College |
| 2017 | Vernon Orioles | Vernon Orioles | Trinity College |
| 2016 | Vernon Orioles | Vernon Orioles | McKenna Field |
| 2015 | Vernon Orioles | Foss Insurance | McKenna Field |
| 2014 | Vernon Orioles | Meriden Merchants | McKenna Field |
| 2013 | Vernon Orioles | Ferguson Waterworks | McKenna Field |
| 2012 | Ferguson Waterworks | Ferguson Waterworks | McKenna Field |
| 2011 | Foss Insurance; People’s United Bank | Ferguson Waterworks | McKenna Field |
| 2010 | Bristol Merchants | Meriden Merchants | McKenna Field |
| 2009 | Bristol Merchants | Bristol Merchants | McKenna Field |
| 2008 | Vernon Orioles | Meriden ProCare | McKenna Field |
| 2007 | Bristol Merchants; People’s Bank | Bristol Merchants | McKenna Field |
| 2006 | Bristol Merchants; Vernon Orioles; Meriden ProCare | People’s Bank | McKenna Field |
| 2005 | Bristol Merchants; Foss Insurance | Bristol Merchants | McKenna Field |
| 2004 | Vernon Orioles | Bristol Merchants | McKenna Field |
| 2003 | Newman Lincoln-Mercury | Newman Lincoln-Mercury | McKenna Field |
| 2002 | Mr. G’s | People’s Bank | McKenna Field |
| 2001 | People’s Bank | People’s Bank | McKenna Field |
| 2000 | Newman Lincoln-Mercury | People’s Bank | McKenna Field |
| 1999 | Newman Lincoln-Mercury | Vernon Orioles | McKenna Field |
| 1998 | Newington Capitols; East Hartford Jets | Newington Capitols | McKenna Field |
| 1997 | Newington Capitols | Newman Lincoln-Mercury | McKenna Field |
| 1996 | East Hartford Jets | Vernon Orioles | McKenna Field |
| 1995 | Newington Capitols | Newman Lincoln-Mercury | Mount Nebo Park |
| 1994 | Newington Capitols | Newman Lincoln-Mercury | Mount Nebo Park |
| 1993 | East Hartford Jets | Society For Savings | Mount Nebo Park |
| 1992 | East Hartford Jets | Newington Capitols | Mount Nebo Park |
| 1991 | Newington Capitols | Newington Capitols | Mount Nebo Park |
| 1990 | Newington Capitols | Newington Capitols | Mount Nebo Park |
| 1989 | Newington Capitols | Newington Capitols | Mount Nebo Park |
| 1988 | Moriarty Brothers | Moriarty Brothers | Palmer Field |
| 1987 | Superior Ford | Newington Capitols | Mount Nebo Park |
| 1986 | Malloves Jewelers | Malloves Jewelers | Mount Nebo Park |
| 1985 | Moriarty Brothers | Society For Savings | Mount Nebo Park |
| 1984 | Society For Savings | Moriarty Brothers | Palmer Field |
| 1983 | Society For Savings | Society For Savings | Palmer Field |
| 1982 | Katz Sports Shop | Society For Savings | Willow Brook Park |
| 1981 | Moriarty Brothers; Katz Sports Shop | Katz Sports Shop | St. Thomas Seminary |
| 1980 | Moriarty Brothers | Moriarty Brothers | St. Thomas Seminary |
| 1979 | Society For Savings | Moriarty Brothers | St. Thomas Seminary |
| 1978 | Bristol Cassins | Bristol Cassins | St. Thomas Seminary |
| 1977 | Hartford Jai-Alai | Moriarty Brothers | St. Thomas Seminary |
| 1976 | East Hartford Merchants | Bristol Cassins | St. Thomas Seminary |
| 1975 | Moriarty Brothers | Moriarty Brothers | St. Thomas Seminary |
| 1974 | Moriarty Brothers | Bristol Cassins | St. Thomas Seminary |
| 1973 | Hartford Insurance Group | New Britain Falcons | St. Thomas Seminary |
| 1972 | Hartford Insurance Group | Moriarty Brothers | St. Thomas Seminary |
| 1971 | Moriarty Brothers; New Britain Falcons | Moriarty Brothers | St. Thomas Seminary |
| 1970 | Moriarty Brothers | Moriarty Brothers | Sterling Field |
| 1969 | Moriarty Brothers | Moriarty Brothers | Colt Park |
| 1968 | Herb’s Sport Shop | Moriarty Brothers | Dillon Stadium |
| 1967 | Moriarty Brothers | Moriarty Brothers | Dillon Stadium |
| 1966 | Valco Machine | Hamilton Standard | Dillon Stadium |
| 1965 | Moriarty Brothers | Moriarty Brothers | Dillon Stadium |
| 1964 | Moriarty Brothers | Valco Machine | Colt Park |
| 1963 | Hamilton Standard | Hamilton Standard | Dillon Stadium |
| 1962 | Hamilton Standard | Hamilton Standard | Dillon Stadium |
| 1961 | Valco Machine | Valco Machine | Dillon Stadium |
| 1960 | St. Cyril’s | Valco Machine | Dillon Stadium |
| 1959 | Riley’s Redlegs | Riley’s Redlegs | Dillon Stadium |
| 1958 | Hamilton Standard | Hamilton Standard | Dillon Stadium |
| 1957 | St. Cyril’s | Pratt & Whitney Aircraft | Dillon Stadium |
| 1956 | Bloomfield Townies | St. Cyril’s | Dillon Stadium |
| 1955 | Pratt & Whitney Aircraft | Hamilton Standard | Municipal Stadium |
| 1954 | Pratt & Whitney Aircraft | Pratt & Whitney Aircraft | Municipal Stadium |
| 1953 | Pratt & Whitney Aircraft; Puritan Maids | Pratt & Whitney Aircraft | Municipal Stadium |
| 1952 | Manchester British-Americans | Wethersfield A.C. | Municipal Stadium |
| 1951 | St. Cyril’s | St. Cyril’s | Colt Park |
| 1950 | Nutmeg Dukes | Nutmeg Dukes | Colt Park |
| 1949 | Columbia A.C. | Columbia A.C. | Bulkeley Stadium |
| 1948 | West Hartford Merchants | West Hartford Merchants | Bulkeley Stadium |
| 1947 | Lenny’s Yellow Taxi | Lenny’s Yellow Taxi | Bulkeley Stadium |
| 1946 | Lenny’s Yellow Taxi | West Hartford Legion | Colt Park |
