Massachusetts State “50+” Softball Singles Champions — Men
| Year | Champion |
| 2015 | Scott Poirier |
| 2014 | Syed Jafry |
| 2013 | Willard Bigelow |
| 2012 | Willard Bigelow |
| 2011 | Robert Brownell |
| 2010 | Willard Bigelow |
| 2009 | Willard Bigelow |
| 2008 | Derrick Niederman |
| 2007 | Derrick Niederman |
| 2006 | Derrick Niederman |
| 2005 | Derrick Niederman |
| 2004 | Malcolm Davidson |
| 2003 | Malcolm Davidson |
| 2002 | Malcolm Davidson |
| 2001 | Malcolm Davidson |
| 2000 | Hoyt Taylor |
| 1999 | Hoyt Taylor |
| 1998 | Hoyt Taylor |
| 1997 | Jay Healy |
| 1996 | Thomas M. Poor |
| 1995 | Leonard A. Bernheimer |
| 1994 | Leonard A. Bernheimer |
| 1993 | John Wheeler |