Consecutive Championships
| School | No. | Year |
| Greely | 6 | 2001-2006 |
| Scarborough | 8 | 2005-2012 |
| Year | No Classes, Class A | Class B |
| 1979 | Ellsworth | |
| Class A | Class B | |
| 1980 | Waterville | Mount Desert |
| 1981 | Brewer | Mount Desert |
| 1982 | Brewer | Mount Desert |
| 1983 | Brewer | Old Town |
| 1984 | South Portland | Scarborough |
| 1985 | South Portland | Ellsworth |
| 1986 | Thornton Academy | Scarborough |
| 1987 | Brewer | Hampden Academy |
| 1988 | Brewer | Hampden Academy |
| 1989 | Thornton Academy | Ellsworth |
| 1990 | Deering | Old Town |
| 1991 | Portland | Greely |
| 1992 | South Portland | Greely |
| 1993 | Mt. Ararat | Greely |
| 1994 | Mt. Ararat | Scarborough |
| 1995 | Thornton Academy | Scarborough |
| 1996 | Thornton Academy | Greely |
| 1997 | Mt. Ararat | Greely |
| 1998 | Brewer | Greely |
| 1999 | Brewer | Scarborough |
| 2000 | Waterville | Hampden |
| 2001 | Waterville | Greely |
| 2002 | Waterville | Greely |
| 2003 | Thornton | Greely |
| 2004 | Thornton | Greely |
| 2005 | Scarborough | Greely |
| 2006 | Scarborough | Greely |
| 2007 | Scarborough | Waterville |
| 2008 | Scarborough | Greely |
| 2009 | Scarborough | Waterville |
| 2010 | Scarborough | York |
| 2011 | Scarborough | Waterville |
| 2012 | Scarborough | Waterville |
| 2013 | Bangor | Waterville |
| 2014 | Thornton | Waterville |
| 2015 | Thornton | Waterville |
| 2016 | Edward Little | Orono |
| 2017 | Scarborough | Greely |
| 2018 | Cheverus-Scarborough-Tie | Greely |
| 2019 | Cheverus | Brewer |