Past DMSL Champions
| YEAR | PIECUSH CHAMPIONS | DIVISION CHAMPIONS | PLAYOFF CHAMPIONS |
| 2013 | Dover Brickhouse | Dover Brickhouse | Dover Brickhouse |
| 2012 | Coolidge Construction | Coolidge Construction | Coolidge Construction |
| 2011 | Coolidge Construction | Coolidge Construction | Coolidge Construction |
| 2010 | EnviroVantage/Cartelli's | EnviroVantage/Cartelli's | EnviroVantage/Cartelli's |
| 2009 | Bud Light/Brickhouse | EnviroVantage/Cartelli's | EnviroVantage/Cartelli's |
| 2008 | Bud Light/Castaways | Dover Brickhouse | |
| 2007 | Coolidge Construction | Ben's Auto Body (Daniels) | Cartelli's Bar & Grill |
| 2006 | Coolidge Construction | Cartelli's Bar & Grill | Cartelli's Bar & Grill |
| 2005 | Coolidge Construction | Daniel's Sports Bar | |
| 2004 | Coolidge Construction | Daniel's Sports Bar | |
| 2003 | Daniel's Sports Bar | Daniel's Sports Bar | |
| 2002 | Coolidge Construction | Coolidge Construction | |
| 2001 | Duston's Market | Sherburne Landscape (Coolidge) | |
| 2000 | Sherburne Landscape (Coolidge) | Sherburne Landscape (Coolidge) |
