Massachusetts State “45+” Softball Singles Champions — Men
| Year | Champion |
| 2015 | Ben W. Willwerth |
| 2014 | Scott Poirier |
| 2013 | Matthew A. Munich |
| 2012 | Matthew A. Munich |
| 2011 | Chris Spahr |
| 2010 | Scott Poirier |
| 2009 | Willard Bigelow |
| 2008 | Philip Constable |
| 2007 | Rob Tittmann |
| 2006 | Philip Constable |
| 2005 | Whitney S. Boucher |
| 2004 | Tim Bacon |
| 2003 | Tim Bacon |
| 2002 | Ron Beck |
| 2001 | Ron Beck |
| 2000 | Malcolm Davidson |
| 1999 | Ron Beck |
| 1998 | Malcolm Davidson |
| 1997 | Malcolm Davidson |
| 1996 | Malcolm Davidson |
| 1995 | John Fulham |
| 1994 | Leonard A. Bernheimer |
| 1993 | Thomas M. Poor |
| 1992 | Leonard A. Bernheimer |