| Year | Location |
| 2024 | Shelton (District 3) |
| 2023 | Trumbull (District 2) |
| 2022 | East Lyme (District 10) |
| 2021 | Springdale (Stamford) (District 1) |
| 2020 | International tournament not held due to Covid-19 pandemic |
| 2019 | Willimantic (District 11) |
| 2018 | East Lyme (District 10) |
| 2017 | Guilford (District 9) |
| 2016 | Manchester (District 8) |
| 2015 | Newington (District 7) |
| 2014 | Harwinton (District 6) |
| 2013 | Southington Southern (District 5) |
| 2012 | Annex (New Haven) (District 4) |
| 2011 | Prospect (District 3) |
| 2010 | North End (Bridgeport) (District 2) |
| 2009 | Springdale (Stamford) (District 1) |
| 2008 | Thompson (District 11) |
| 2007 | Waterford South (District 10) |
| 2006 | Haddam (District 9) |
| 2005 | Manchester (District 8) |
| 2004 | Newington (District 7) |
| 2003 | Thomaston (District 6) |
| 2002 | Wallingford (District 5) |
| 2001 | Orange (District 4) |
| 2000 | Shelton National (District 3) |
| 1999 | North End (Bridgeport) (District 2) |
| 1998 | Stamford Federal (District 1) |
| 1997 | East Hampton (District 9) |
| 1996 | Little League Baseball Eastern Region Headquarters (Bristol) (District 5) |
| 1995 | Little League Baseball Eastern Region Headquarters (Bristol) (District 5) |
| 1994 | Little League Baseball Eastern Region Headquarters (Bristol) (District 5) |
| 1993 | Little League Baseball Eastern Region Headquarters (Bristol) (District 5) |
| 1992 |
Division 1 - Little League Baseball Eastern Region Headquarters (Bristol)
(District 5) Division 2 - Pawcatuck (District 10) |
| 1991 |
Division 1 - Trumbull
(District 2) Division 2 - Cromwell (District 9) |
| 1990 |
Division 1 - Shelton
(District 3) Division 2 - East Hartford (District 7) |
| 1989 |
Division 1 - (Unknown)
Division 2 - Cromwell (District 9) |
| 1988 |
Division 1 - Darien
(District 1) Division 2 - Darien (District 1) |
| 1987 |
Division 1 - Berlin
(District 5) Division 2 - Berlin (District 5) |
| 1986 | Waterford (District 10) |
| 1985 | Trumbull (District 2) |
| 1984 | Peter J. Foley (Naugatuck) (District 3) |
| 1983 | Simsbury (District 6) |
| 1982 | Thompson (District 11) |
| 1981 | Middletown (District 9) |
| 1980 | Newington (District 7) |
| 1979 | Poquonnock (District 10) |
| 1978 | Annex (New Haven) (District 4) |
| 1977 | Ridgefield (District 1) |
| 1976 | Wallingford (District 5) |
| 1975 | New London National (District 10) |
| 1974 | Stratford (District 2) |
| 1973 | Peter J. Foley (Naugatuck) (District 3) |
| 1972 | Simsbury (District 6) |
| 1971 |
Division 1 - Springdale (Stamford)
(District 1) Division 2 - South Windsor (District 8) |
| 1970 | Norwich (District 11) |
| 1969 | Middletown (District 9) |
| 1968 | Windsor Locks (District 8) |
| 1967 | Annex (New Haven) (District 4) |
| 1966 | Springdale (Stamford) (District 1) |
| 1965 | Forestville (District 5) |
| 1964 | New London (District 10) |
| 1963 | Black Rock (Bridgeport) (District 2) |
| 1962 | Peter J. Foley (Naugatuck) (District 3) |
| 1961 | Simsbury (District 6) |
| 1960 | Norwich (District 11) |
| 1959 | Middletown (District 9) |
| 1958 | Rockville (District 8) |
| 1957 | Milford (District 3) |