The Jim McGregor Tropy
Jim McGregor Trophy
Final Tournament Champions
Presented to the Year-End Tournament Champion
| Year | Champion |
| 2011 | Northtown Sox |
| 2010 | EM Automotive Sox |
| 2009 | Red Hot Dawgs |
| 2008 | Red Hot Dawgs |
| 2007 | Markham Knights |
| 2006 | Remax Crush |
| 2005 | EM Automotive Sox |
| 2004 | Markham Knights |
| 2003 | Col. Mustards Athletics |
| 2002 | Col. Mustards Athletics |
| 2001 | Fox & Fiddle |
| 2000 | Northtown Auto Centre |
| 1999 | Col. Mustards Athletics |
| 1998 | Markham Chrysler |
| 1997 | Buttonville Esso |
| 1996 | Markham Chrysler |
| 1995 | Foremost Financial / Markham Vision |
| 1994 | |
| 1993 | Fenway's Braves |
| 1992 | Fenway's Braves |
| 1991 | Lube 'N' Zoom |
| 1990 | The Village Grocer |
| 1989 | Ethier Cribari |
| 1988 | Toni Sullivan Remax |
| 1987 | Barry's Auto |
| 1986 | Hogan Chev Olds |
| 1985 | Unionville Motors |
| 1984 | Carson & Weeks |
| 1983 | Century 21 / Sylvia Houghton |
| 1982 | Susan Moon |
| 1981 | North Sherwood Shell |
| 1980 | North Sherwood |
| 1979 | Sherwood Green |
| 1978 | Sherwood Green |
| 1977 | East Markham |
| 1976 | Sherwood North |
| 1975 | Sherwood Green |
| 1974 | East Markham |
| 1973 | Unionville Vets |
| 1972 | Sherwood North |
| 1971 | Unionville |
| 1970 | Unionville |
| 1969 | Sherwood Estates |