| Year | Location |
| 2009 | Milton (District 3) |
| 2008 | Brattleboro (District 2) |
| 2007 | Barre Community Baseball (District 4) |
| 2006 | North Burlington (District 1) |
| 2005 | Essex Town (District 3) |
| 2004 | Bennington (District 2) |
| 2003 | Barre Community Baseball (District 4) |
| 2002 | South Burlington (District 1) |
| 2001 | Essex (District 3) |
| 2000 | Bennington (District 2) |
| 1999 | St. Johnsbury (District 4) |
| 1998 | North Burlington (District 1) |
| 1997 | St. Albans (District 3) |
| 1996 | Bennington (District 2) |
| 1995 | Barre Community Baseball (District 4) |
| 1994 | North Burlington (District 1) |
| 1993 | St. Albans (District 3) |
| 1992 | Brattleboro (District 2) |
| 1991 | St. Johnsbury (District 1) |
| 1990 | North Burlington (Area 2) |
| 1989 | St. Albans (Area 1) |
| 1988 | Barre (Area 3) |
| 1987 | Barre City (Area 3) |
| 1986 | Bennington (Area 5) |
| 1985 | St. Johnsbury (Area 4) |
| 1984 | Barre City (Area 3) |
| 1983 | Brattleboro (Area 5) |
| 1982 | Green Mountain (Barre Town) (Area 3) |
| 1981 | Granite City (Barre) (Area 3) |
| 1980 | Barre City (Area 3) |
| 1979 | Bennington (Area 4) |
| 1978 | Barre City (Area 3) |
| 1977 | Granite City (Barre) (Area 3) |
| 1976 | Bennington |
| 1975 | Barre City |
| 1974 | Brattleboro |
| 1973 | Barre City |
| 1972 | Bennington |
| 1971 | Granite City (Barre) |
| 1970 | Brattleboro |
| 1969 | Montpelier |
| 1968 | Brattleboro |
| 1967 | Montpelier |
| 1966 | Granite City (Barre) |
| 1965 | Granite City (Barre) |
| 1964 | Brattleboro |
| 1963 | Burlington American |
| 1962 | Brattleboro |
| 1961 | Brattleboro |
| 1960 | Granite City (Barre) |
| 1959 | North Bennington |
| 1958 | Burlington American |
| 1957 | North Bennington |