Massachusetts State “5.5” Singles Champions – Men
| Year | Champion |
| 2015 | Mark M. Froot |
| 2014 | Carson Spahr |
| 2013 | John Roberts |
| 2012 | Daniel Sharplin |
| 2011 | Daniel Sharplin |
| 2010 | Daniel Sharplin |
| 2009 | Daniel Sharplin |
| 2008 | Preston Quick |
| 2007 | Preston Quick |
| 2006 | Daniel Sharplin |
| 2005 | Daniel Sharplin |
| 2004 | Daniel Sharplin |
| 2003 | Lucky Odeh |
| 2002 | Lucky Odeh |
| 2001 | Ron Rubin |
| 2000 | Pat Malloy |
| 1999 | Doug Lifford |