Massachusetts State “40+” Softball Singles Champions — Men
| Year | Champion |
| 2015 | Charles W. Humber |
| 2014 | Ben W. Willwerth |
| 2013 | Ben W. Willwerth |
| 2012 | Ben W. Willwerth |
| 2011 | Doug Lifford |
| 2010 | Doug Lifford |
| 2009 | Tyler Hindermann |
| 2008 | David Bennett |
| 2007 | David Bennett |
| 2006 | David Bennett |
| 2005 | Tyler Hindermann |
| 2004 | Tyler Hindermann |
| 2003 | Philip Constable |
| 2002 | Bob Brownell |
| 2001 | Philip Constable |
| 2000 | Ron Beck |
| 1999 | Ron Beck |
| 1998 | Jeffrey L. Randall |
| 1997 | Malcolm Davidson |
| 1996 | Jeffrey L. Randall |
| 1995 | Malcolm Davidson |
| 1994 | John Connolly |
| 1993 | Chris Burr |