Consecutive Championships
| School | No. | Year |
| Chevrus | 7 | 1980-1986 |
| Scarborough | 5 | 1994-1998 |
————————————————————————————-
| Year | No Classes, Class A | Class B |
| 1968 | Portland | |
| 1969 | Deering | |
| 1970 | Portland | |
| 1971 | South Portland | |
| 1972 | South Portland | |
| Class A | Class B | |
| 1973 | Deering | Lawrence |
| 1974 | Deering | Lawrence |
| 1975 | Deering/Brunswick (Tie) | Lawrence |
| 1976 | Portland | Orono |
| 1977 | Portland | Cheverus |
| 1978 | Portland | Cheverus |
| 1979 | Portland | Lawrence |
| 1980 | Cheverus | Lawrence |
| 1981 | Cheverus | Lawrence |
| 1982 | Cheverus | Lawrence/Orono (Tie) |
| 1983 | Cheverus | Bucksport/Scarborough (Tie) |
| 1984 | Cheverus | Cape Elizabeth |
| 1985 | Cheverus | Ellsworth |
| 1986 | Cheverus | Scarborough |
| 1987 | Deering | Hampden |
| 1988 | Cheverus | Hampden Academy |
| 1989 | Cheverus | Ellsworth |
| 1990 | Cheverus | Scarborough |
| 1991 | Brunswick | Scarborough |
| 1992 | Cheverus | Greely |
| 1993 | Cheverus | Greely |
| 1994 | Old Town | Scarborough |
| 1995 | Cheverus | Scarborough |
| 1996 | Brewer | Scarborough |
| 1997 | Cheverus | Scarborough |
| 1998 | Cheverus | Scarborough |
| 1999 | South Portland | Gorham |
| 2000 | South Portland | Scarborough |
| 2001 | South Portland | Scarborough |
| 2002 | South Portland | Ellsworth |
| 2003 | Deering | Greely |
| 2004 | Deering | Gorham |
| 2005 | Portland | Gorham |
| 2006 | Bonny Eagle | Falmouth |
| 2007 | Bangor | Falmouth |
| 2008 | Brunswick | Falmouth |
| 2009 | Scarborough | Greely |
| 2010 | Brunswick | Falmouth |
| 2011 | Scarborough | Falmouth |
| 2012 | Scarborough | York |
| 2013 | Scarborough | York |
| 2014 | Scarborough | Waterville |
| 2015 | Falmouth | York |
| 2016 | Scarborough | York |
| 2017 | Scarborough | Mt. Desert |
| 2018 | Scarborough | Greely |
| 2019 | Scarborough | York |