Consecutive Champions
| 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