League Champions
| Year | Team |
| 2023 | Tri-Town Trojans defeated Bethlehem Plowboys |
| 2022 | Tri-Town Trojans defeated Bethlehem Plowboys |
| 2021 | Tri-Town Trojans defeated Terryville Black Sox |
| 2020 | No Season – Covid |
| 2019 | Terryville Black Sox defeated Naugatuck Dogs |
| 2018 | Tri-Town Trojansdefeated Terryville Black Sox |
| 2017 | Naugatuck Dogs defeated Tri-Town Trojans |
| 2016 | Watertown Blaze defeated Naugatuck Dogs |
| 2015 | Litchfield Cowboys defeated Tri-Town Trojans |
| 2014 | Wolcott Scrappers defeated Tri-Town Trojans |
| 2013 | Tri-Town Trojans defeated Naugatuck Dogs |
| 2012 | Litchfield Cowboys defeated Waterbury Wild |
| 2011 | Litchfield Cowboys defeated Tri-Town Trojans |
| 2010 | Bethlehem Plowboys defeated Tri-Town Trojans |
| 2009 | Brass City Brew defeated Bethlehem Plowboys |
| 2008 | Winsted Whalers defeated Brass City Brew |
| 2007 | Torrington Rebels defeated Bethlehem Plowboys |
| 2006 | Torrington Rebels defeated Bethlehem Plowboys |
| 2005 | Bethlehem Plowboys defeated Torrington Rebels |
| 2004 | Torrington Rebels defeated Tribury Turkey Vultures |
| 2003 | Thomaston Spoilers defeated Bethlehem Plowboys |
| 2002 | Bethlehem Plowboys defeated Winsted Thunder |
| 2001 | Bethlehem Plowboys defeated Winsted Thunder |
| 2000 | Terryville Titans defeated Winsted Thunder |
| 1999 | Bethlehem Plowboys defeated Thomaston Spoilers |
| 1998 | Bethlehem Plowboys defeated Lakeville Firemen |
| 1997 | Torrington Rebels defeated Bethlehem Plowboys |
| 1996 | Terryville Titans defeated Bethlehem Plowboys |
| 1995 | Torrington Rebels defeated Lakeville Firemen |
| 1994 | Torrington Rebels defeated Winsted Lightning |
| 1993 | Torrington Rebels defeated Amenia Monarchs |
| 1992 | Torrington Rebels defeated Amenia Monarchs |
| 1991 | Pine Plains Drifters defeated Thomaston Spoilers |
| 1990 | Amenia Monarchs defeated Litchfield Cowboys |
| 1989 | Thomaston Spoilers defeated Amenia Monarchs |
| 1988 | Amenia Monarchs defeated Winsted Warriors |
| 1987 | Winsted Warriors defeated Amenia Monarchs |
| 1986 | Winsted Warriors defeated Amenia Monarchs |
| 1985 | Amenia Monarchs defeated Litchfield Cowboys |
| 1984 | Amenia Monarchs defeated Winsted Warriors |
| 1983 | Amenia Monarchs defeated Lakeville Firemen |
| 1982 | Amenia Monarchs defeated Winsted Warriors |
| 1981 | Lakeville Firemen defeated Amenia Monarchs |
| 1980 | Lakeville Firemen defeated Amenia Monarchs |
| 1979 | Litchfield Cowboys defeated Washington/Shepaug |
| 1978 | Winsted Whalers defeated Litchfield Cowboys |
| 1977 | Amenia Monarchs defeated Lakeville Firemen |
| 1976 | Lakeville Firemen defeated Amenia Monarchs |
| 1975 | Lakeville Firemen defeated Winsted Warriors |
| 1974 | Amenia Monarchs defeated Winsted Warriors |
| 1973 | Lakeville Firemen defeated Winsted Warriors |
| 1972 | Winsted Warriors defeated Lakeville Firemen |
| 1971 | Winsted Warriors defeated Amenia Monarchs |
| 1970 | Lakeville Firemen defeated Winsted Warriors |
| 1969 | Amenia Monarchs defeated Lakeville Firemen |
| 1968 | Amenia Monarchs defeated Winsted Warriors |
NOTE: During the late 60’s and early 70’s; a second league, named the Pomperaug Valley League, co-existed and included a few Tri-State League teams. Lakeville was the perennial champion before losing to Roxbury for two consecutive seasons in the early 70’s.