Tennis Court at Lakewood resort in East Madison (2005)
Consecutive Championships
| School |
No. |
Year |
| Lewiston | 7 | 2003-2009 |
| South Portland | 4 | 1973-1976 |
| Cape Elizabeth | 4 | 1986-1989 |
| Cheverus | 4 | 1988-1991 |
| Waynflete | 12 | 2008-2019 |
| YEAR | No Classes | YEAR | Class A | Class B | Class C | |
| 1956 | Brunswick | 1983 | Lewiston | York | ||
| 1960 | South Portland | 1984 | Lewiston | York | ||
| 1961 | South Portland | 1985 | Cape Elizabeth | York | ||
| 1962 | Brunswick | 1986 | Waterville | Cape Elizabeth | ||
| 1963 | South Portland | 1987 | Lewiston | Cape Elizabeth | ||
| 1964 | South Portland/Brunswick | 1988 | Cheverus | Cape Elizabeth | ||
| 1965 | South Portland | 1989 | Cheverus | Cape Elizabeth | ||
| 1966 | South Portland | 1990 | Cheverus | York | ||
| 1967 | Portland | 1991 | Cheverus | Camden-Rockport | ||
| 1968 | n.a. | 1992 | Lewiston | Camden-Rockport | ||
| 1969 | Yarmouth | 1993 | Cony | Cape Elizabeth | ||
| 1970 | Portland | 1994 | Lewiston | Cape Elizabeth | ||
| 1971 | South Portland | 1995 | Lewiston | Cape Elizabeth | Falmouth | |
| 1972 | Cony | 1996 | Brunswick | Ellsworth | Yarmouth | |
| 1973 | South Portland | 1997 | Brunswick | Cape Elizabeth | Falmouth | |
| 1974 | South Portland | 1998 | Waterville | Hampden | Falmouth | |
| 1975 | South Portland | 1999 | Brunswick | Fryeburg | Madawaska | |
| 1976 | South Portland | 2000 | Deering | York | Waynflete | |
| 1977 | Yarmouth | 2001 | Deering | Greely | Winthrop | |
| 1978 | Yarmouth | 2002 | Bangor | Cape Elizabeth | Waynflete | |
| 1979 | South Portland | 2003 | Lewiston | Cape Elizabeth | North Yarmouth | |
| 1980 | South Portland | 2004 | Lewiston | Cape Elizabeth | North Yarmouth | |
| 1981 | South Portland | 2005 | Lewiston | Camden Hills | Waynflete | |
| 1982 | Lewiston | 2006 | Lewiston | Falmouth | Waynflete | |
| 2007 | Lewiston | Falmouth | North Yarmouth | |||
| 2008 | Lewiston | Caribou | Waynflete | |||
| 2009 | Lewiston | Yarmouth | Waynflete | |||
| 2010 | Windham | Cape Elizabeth | Waynflete | |||
| 2011 | Lewiston | Falmouth | Waynflete | |||
| 2012 | Gorham | Falmouth | Waynflete | |||
| 2013 | Gorham | Cape Elizabeth | Waynflete | |||
| 2014 | Falmouth | Cape Elizabeth | Waynflete | |||
| 2015 | Falmouth | Cape Elizabeth | Waynflete | |||
| 2016 | Thornton | Camden | Waynflete | |||
| 1017 | Falmouth | Camden | Waynflete | |||
| 2018 | Falmouth | Caribou | Waynflete | |||
| 2019 | Falmouth | Yarmouth | Waynflete | |||
| Source: Maine Principals Association |
| Portland |