2024 - Milford
2023 - Orange
2022 - Orange
2021 - Max Sinoway (North Haven)
2020 - International tournament not held due to Covid-19 pandemic
2019 - Max Sinoway (North Haven)
2018 - Milford National Lou Gehrig
2017 - North Branford
2016 - Milford National Lou Gehrig
2015 - Hamden Fathers
2014 - Annex (New Haven)
2013 - Orange
2012 - Annex (New Haven)
2011 - East Haven
2010 - Orange
2009 - Hamden Fathers
2008 - North Branford
2007 - Annex (New Haven)
2006 - Ron Bernardini (Hamden)
2005 - Milford National Lou Gehrig
2004 - Hamden
2003 - Hamden
2002 - Orange
2001 - Branford
2000 - Orange
1999 - North Branford
1998 - West Haven American
1997 - Annex (New Haven)
1996 - Branford
1995 - Orange
1994 - Jackie Vets (Hamden)
1993 - Orange
1992 - Hamden South
1991 - Walter "Pop" Smith (New Haven)
1990 - Hamden
1989 - Ron Bernardini (Hamden)
1988 - Walter "Pop" Smith (New Haven)
1987 - Hamden
1986 - Ron Bernardini (Hamden)
1985 - Ron Bernardini (Hamden)
1984 - West Haven American
1983 - Jackie Vets (Hamden)
1982 - Walter "Pop" Smith (New Haven)
1981 - Annex (New Haven)
1980 - Walter "Pop" Smith (New Haven)
1979 - West Haven
1978 - Walter "Pop" Smith (New Haven)
1977 - Milford International
1976 - West Haven
1975 - North Branford
1974 - Walter "Pop" Smith (New Haven)
1973 - Milford American
1972 - Orange
1971 - New Haven Annex
1970 - Annex (New Haven)
1969 - Milford American
1968 - Walter "Pop" Smith (New Haven)
1967 - North Haven
1966 - North Haven National
1965 - Walter "Pop" Smith (New Haven)
1964 - Branford
1963 - Milford National
1962 - Walter "Pop" Smith (New Haven)
1961 - North Branford
1960 - North Haven
1959 - Milford American
1958 - North Haven
1957 - McCabe-Waters (Bristol)

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