| Year | Location |
| 2008 | Joe Schwartz (Worcester) (District 4) |
| 2007 | Pittsfield (District 1) |
| 2006 | Oxford (District 5) |
| 2005 | Beverly (District 15) |
| 2004 | Middleboro (District 7) |
| 2003 | Oxford (District 5) |
| 2002 | Adams (District 1) |
| 2001 | Wyoma (Lynn) (District 16) |
| 2000 | Beverly (District 15) |
| 1999 | Leominster American (District 3) |
| 1998 | Taunton Western (District 6) |
| 1997 | Parkway National (West Roxbury) (District 10) |
| 1996 | Easthampton (District 2) |
| 1995 | Beverly (District 15) |
| 1994 | Oxford (District 5) |
| 1993 | Oxford (District 5) |
| 1992 | Stoughton (District 8) |
| 1991 | Pittsfield South (District 1) |
| 1990 | Leominster American (District 3) |
| 1989 | Wyoma (Lynn) (District 16) |
| 1988 | Billerica (District 14) |
| 1987 | Athol (District 3) |
| 1986 | Westfield South (District 2) |
| 1985 | Millis (District 11) |
| 1984 | Swampscott (District 16) |
| 1983 | Leominster American(District 3) |
| 1982 | Athol (District 3) |
| 1981 | Downey Memorial (Brockton) (District 7) |
| 1980 | Parkway (West Roxbury) |
| 1979 | Tewksbury (District 14) |
| 1978 | Wakefield (District 13) |
| 1977 | Joe Schwartz (Worcester) (District 4) |
| 1976 | Danvers (District 15) |
| 1975 | Pittsfield South (District 1) |
| 1974 | Taunton (District 6) |
| 1973 | Easthampton (District 2) |
| 1972 | Newburyport (District 14) |
| 1971 | Plymouth (District 7) |
| 1970 | Oxford (District 5) |
| 1969 | Brighton |
| 1968 | Joe Schwartz (Worcester) (District 4) |
| 1967 | Weymouth (District 7) |
| 1966 | East Longmeadow (District 2) |
| 1965 | Joe Schwartz (Worcester) (District 4) |
| 1964 | Orange (District 3) |
| 1963 | Danvers (District 15) |
| 1962 | Braintree (District 9) |
| 1961 | Haverhill American (District 16) |
| 1960 | East Longmeadow (District 2) |
| 1959 | Franklin (District 6) |
| 1958 | Franklin (District 6) |
| 1957 | Franklin |