School | No. | Year |
Madison | 4 | 1994-1997 |
Traip | 3 | 1988-1990 |
Jonesport-Beals | 3 | 1992-1994 |
Richmond | 4 | 2013-2016 |
Year | Class A | Class B | Class C | Class D |
1977 | Winslow | Hermon | Massabesic | |
1978 | Mt. Ararat | Gorham | Searsport | |
1979 | Winslow | Massabesic | Madison | |
1980 | Gardiner | Van Buren | York | |
1981 | Westbrook | Gorham | Mexico | |
1982 | Houlton | Lisbon | Mexico | |
1983 | Cony | Gorham | Traip | |
1984 | Portland | Bucksport | Gray-New Gloucester | |
1985 | Deering | Leavitt | Central | |
1986 | Deering | Bucksport | Sacopee | Buckfield |
1987 | Portland | Bucksport | Sacopee | Buckfield |
1988 | Deering | York | Traip | Katahdin |
1989 | Deering | York | Traip | Katahdin |
1990 | Portland | Lisbon | Traip | Buckfield |
1991 | Portland | Messalonskee | Telstar | Buckfield |
1992 | Bonny Eagle | Lisbon | Madison | Jonesport-Beals |
1993 | Skowhegan | Winslow | Falmouth | Jonesport-Beals |
1994 | Portland | Oak Hill | Madison | Jonesport-Beals |
1995 | Medomak Valley | Windham | Madison | Richmond |
1996 | Edward Little | Gorham | Madison | Ashland |
1997 | Edward Little | Scarborough | Madison | Monmouth |
1998 | Oxford Hills | Winslow | Searsport | Monmouth |
1999 | Oxford Hills | Maranacook | Jay | Buckfield |
2000 | Portland | Erskine | Mattanawcook | Monmouth |
2001 | Portland | Gray-New Gloucester | St. Dominic | Monmouth |
2002 | Leavitt | Greely | Narraguagus | Buckfield |
2003 | Leavitt | Gray-New Gloucester | Sacopee Valley | Buckfield |
2004 | Portland | Winslow | Sacopee Valley | Richmond |
2005 | Messalonskee | Winslow | Central | Richmond |
2006 | Biddeford | Bucksport | Telstar | Lee |
2007 | Scarborough | Cape Elizabeth | Georges Valley | Buckfield |
2008 | Brewer | Fryeburg | Georges Valley | Buckfield |
2009 | Scarborough | Fryeburg | Calais | Woodland |
2010 | South Portland | Hermon | Telstar | Richmond |
2011 | Scarborough | Freyburg | Telstar | Deer Isle – Stonington |
2012 | Cony | Old Town | Bucksport | Penobscot Valley |
2013 | Scarborough | Oceanside | Bucksport | Richmond |
2014 | Skowhegan | Hermon | Madison | Richmond |
2015 | Messalonskee | Yarmouth | Bucksport | Richmond |
2016 | Biddeford | Old Town | Madison | Richmond |
2017 | Scarborough | Old Town | Bucksport | Penobscot Valley |
2018 | Scarborough | Brewer | Madison | Greenville |
2019 | Scarborough | Brewer | Madison | Penobscot Valley |
Source: Maine Principals Association and news accounts