Consecutive Championships
| School | No. | Year |
| North Yarmouth | 5 | 2003-2007 |
| Year | No Class | Class B | Class C | Class D | |
| 1980 | Waterville | ||||
| 1981 | Waterville | ||||
| Class A | |||||
| 1982 | Waterville | Hyde | |||
| 1983 | Waterville | Penobscot Valley | |||
| 1984 | Waterville | Penquis Valley | |||
| 1985 | Mount Ararat | Penobscot Valley | |||
| 1986 | Caribou | Penobscot Valley | |||
| 1987 | Mount Ararat | Houlton | Carrabec | ||
| 1988 | Cape Elizabeth | York | Schenck | ||
| 1989 | Cape Elizabeth | Fryeburg Academy | Van Buren | Ashland | |
| 1990 | Westbrook | York | Schenck | Katahdin | |
| 1991 | Mount Ararat | Lisbon | Schenck | Van Buren | |
| 1992 | Mt. Ararat | York | Falmouth | Richmond | |
| 1993 | Mt. Ararat | Windham | Schenck | Richmond | |
| 1994 | Greely | Windham | Katahdin | Richmond | |
| 1995 | Deering | Yarmouth | Falmouth | Waynflete | |
| 1996 | Cape Elizabeth | Mt. View | Dirigo | Waynflete | |
| 1997 | Cape Elizabeth | Mt. Desert | Madawaska | Waynflete | |
| 1998 | Deering | Scarborough | Falmouth | Richmond | |
| 1999 | Cape Elizabeth | Scarborough | North Yarmouth | Van Buren | |
| 2000 | Greely | Winslow | North Yarmouth | Monmouth | |
| 2001 | Mt. Ararat | Falmouth | Traip | Richmond | |
| 2002 | Greely | Falmouth | Searsport | Waynflete | |
| 2003 | Mt. Ararat | Yarmouth | North Yarmouth | Lee | |
| 2004 | Brunswick | Gorham | North Yarmouth | Waynflete | |
| 2005 | Gorham | Falmouth | North Yarmouth | Lee | |
| 2006 | Gorham | Falmouth | North Yarmouth | Lee | |
| 2007 | Gorham | York | North Yarmouth | Richmond | |
| 2008 | Waterville | Falmouth | Waynflete | Southern Aroostook | |
| 2009 | Brunswick | York | Georges Valley | So. Aroostook | |
| 2010 | Scarborough | Falmouth | Sacopee Valley | Richmond | |
| 2011 | Bangor | Falmouth | Central | Richmond | |
| 2012 | Scarborough | Falmouth | Waynflete | Richmond | |
| 2013 | Windham | Cape Elizabeth | Waynflete | Washburn | |
| 2014 | Windham | Waterville | Sacopee | Ashland | |
| 2015 | Bangor | Greely | Orono | Richmond | |
| 2016 | Camden Hills | Yarmouth | Orono | Ashland | |
| 2017 | Camden Hills | Yarmouth | Houlton | Richmond | |
| 2018 | Camden Hills | Cape Elizabeth | Fort Kent | Central Aroostook | |
| 2019 | Camden Hills | Cape Elizabeth | Traip | Penobscot |
Source: Maine Principals Association and news accounts.