| 1993 | Charles W. Austin (Orient) | 2008 | Mark William Doane (Berkshire) |
| 1995 | Clayton A. Bemis (Brockton-Abington) | 2009-2010 | Donald R. Denning, Jr. (Orient) |
| 1996 | John C. Sutterley (Temple) | 2011 | Manuel Ferreira, III (Fall River) |
| 1998 | Gerald H. Pass (Cape Cod) | 2012 | Ronald E. Wolf (Berkshire) |
| 2000 | Paul A. Salvas (Temple) | 2013 | David A. Schofield (Cape Cod) |
| 2001 | Donald W. Carriger, Jr. (Orient) | 2014 | Demetrios J. Sarantopoulos (Brockton-Abington) |
| 2002 | John K. Andrews (Hiram) | 2015 (H) | George A. Wiseman (Orient) |
| 2003 | Leo A. Morin, Jr. (Temple) | 2016 | Alexander A. Bird (Orient) |
| 2004 | Wayne L. Robbins (Brockton-Abington) | 2017 | Nathaniel R.J. Ulrich (Boston) |
| 2005 | Charles E. Katsanos (Fall River) | 2018 | Andrew C. Maninos (Orient) |
| 2006 | Peter K. Stone (Cape Cod) | 2019 | Michael S. Bickford (Cryptic) |
