Massachusetts State “55+” Softball Singles Champions — Men
| Year | Champion |
| 2015 | Willard Bigelow |
| 2014 | Willard Bigelow |
| 2013 | Bill Kaplan |
| 2012 | Sam Thayer |
| 2011 | Sam Thayer |
| 2010 | Sam Thayer |
| 2009 | Robert W. Loring |
| 2008 | Robert W. Loring |
| 2007 | Malcolm Davidson |
| 2006 | Malcolm Davidson |
| 2005 | Fran Donlan |
| 2004 | Fran Donlan |
| 2003 | Fran Donlan |
| 2002 | Wayne Hodges |
| 2001 | Fran Donlan |
| 2000 | Daniel Hogan |
| 1999 | Michael Keating |
| 1998 | Kirk Randall |
| 1997 | Ray Rodriguez |
| 1996 | John Wheeler |
| 1995 | Tim Chilton |
| 1994 | Lewis Holmes |
| 1993 | John Wheeler |
| 1992 | John Wheeler |