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MDSL Past Champions
| Year | Regular Season Champion | Playoff Champion |
| 2007 | Fredericktown United (9-1-0) | Fredericktown United |
| 2006 | Fredericktown United (8-1-1) | Fredericktown United |
| 2005 | Fredericktown United (7-1-2) | Bushwaller's FC |
| 2004 | Bushwaller's FC (9-0-0) | Bushwaller's FC |
| 2003 | Bushwaller's FC (8-0-2) | Fredericktown United |
| 2002 | Williamsport SC (8-0-3) | Bushwaller's FC |
| 2001 | Bushwaller's FC (11-0-1) | Waynesboro SC |
| 2000 | Williamsport SC (10-1-1) | Bushwaller's FC |
| 1999 | Bushwaller's FC (8-2) | Bushwaller's FC |
| 1998 | Chambersburg Wings (11-2) | Bushwaller's FC |
| 1997 | Middletown (11-2) | Waynesboro |
| 1996 | Chambersburg Wings (11-2) | Middletown |
| 1995 | Chambersburg Wings (10-1) | Johansson's |
| 1994 | Walkersville SC (10-2-1) | Westminster Wolves |
| 1993 | Mercersburg (11-0) | Chambersburg Wings |
| 1992 | Mercersburg (10-1) | Chambersburg Wings |
| 1991 | Walkersville SC (10-1) | Walkersville SC |
| 1990 | Chambersburg Wings (12-1) | Middletown |
| 1989 | Williamsport (10-2-1) | Chambersburg Wings |
| 1988 | Chambersburg Wings (11-1) | McConnellsburg |
| 1987 | McConnellsburg (11-1-1) | Walkersville SC |
| 1986 | McConnellsburg (10-1) | McConnellsburg |
| 1985 | Williamsport (10-1) | Walkersville SC |
| 1984 | Chambersburg Wings (11-1) | Williamsport |
| 1983 | Chambersburg Wings (11-0-1) | Chambersburg Wings |
| 1982 | Chambersburg Wings (14-0) | Chambersburg Wings |
| 1981 | Walkersville SC (13-1) | St. Thomas |
| 1980 | Walkersville SC (11-1) | St. Thomas |
| 1979 | Chambersburg Wings (10-0-1) | Chambersburg Wings |
| 1978 | Chambersburg Wings (10-0-1) | Chambersburg Wings |
| 1977 | Chambersburg Wings (11-1) | St. Thomas |
| 1976 | Chambersburg Wings (10-1-1) | Middletown |
| 1975 | Williamsport | unknown |
| 1974 | Middletown | unknown |
| 1973 | Williamsport | unknown |
Last Update: March 30, 2007