| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Alex Lester (F) | 1996 | Methuen, MA, USA | - |
| 2 | | Taylor Larsen (F) | 1989 | Newton, MA, USA | - |
| 2 | | Rob Pascale (F) | 1982 | South Portland, ME, USA | - |
| 1 | | Hunter Brackett (F) | 2000 | Miami, FL, USA | - |
| 1 | | Ronny Paragallo (F) | 2001 | Huntington, NY, USA | - |
| 1 | | Conor Foley (F) | 1998 | Nahant, MA, USA | - |
| 1 | | Andrew Andary (F) | 1999 | Macomb, MI, USA | - |
| 1 | | Cam Laughlin (F) | 1994 | Natick, MA, USA | - |
| 1 | | Sam D'Antuono (F) | 1995 | Hingham, MA, USA | - |
| 1 | | Brandon Bete (F) | 1993 | Greenfield, MA, USA | - |
| 1 | |  A.J. Pieprzak (F) | 1992 | Barrie, ON, CAN | - |
| 1 | | Joe Collins (F) | 1992 | Mansfield, MA, USA | - |
| 1 | | Mike Richard (F) | 1989 | Derry, NH, USA | - |
| 1 | | Coleman Noonan (F) | 1989 | Norfolk, MA, USA | - |
| 1 | | Patrick O'Kane (F) | 1989 | Hollis, NH, USA | - |
| 1 | | Troy Maybury (F) | - | South Portland, ME, USA | - |
| 1 | | Ryan Mero (F) | 1985 | Peekskill, NY, USA | - |
| 1 | | Brendan O'Brien (F) | 1984 | Braintree, MA, USA | - |
| 1 | | Jared Silver (F) | 1984 | Montréal, QC, CAN | - |
| 1 | | Pat Doherty (F) | 1982 | Wakefield, MA, USA | - |
| 1 | | Michael Martiniello (F) | 1978 | Wilmington, MA, USA | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 24-25 | | Hunter Brackett (F) | 2000 | Miami, FL, USA | - |
| 23-24 | | Ronny Paragallo (F) | 2001 | Huntington, NY, USA | - |
| 22-23 | | Conor Foley (F) | 1998 | Nahant, MA, USA | - |
| 21-22 | | Andrew Andary (F) | 1999 | Macomb, MI, USA | - |
| 19-20 | | Alex Lester (F) | 1996 | Methuen, MA, USA | - |
| 18-19 | | Alex Lester (F) | 1996 | Methuen, MA, USA | - |
| 17-18 | | Cam Laughlin (F) | 1994 | Natick, MA, USA | - |
| 16-17 | | Sam D'Antuono (F) | 1995 | Hingham, MA, USA | - |
| 15-16 | | Brandon Bete (F) | 1993 | Greenfield, MA, USA | - |
| 14-15 | | A.J. Pieprzak (F) | 1992 | Barrie, ON, CAN | - |
| 13-14 | | Joe Collins (F) | 1992 | Mansfield, MA, USA | - |
| 12-13 | | Mike Richard (F) | 1989 | Derry, NH, USA | - |
| 11-12 | | Taylor Larsen (F) | 1989 | Newton, MA, USA | - |
| 10-11 | | Taylor Larsen (F) | 1989 | Newton, MA, USA | - |
| 09-10 | | Coleman Noonan (F) | 1989 | Norfolk, MA, USA | - |
| 09-10 | | Patrick O'Kane (F) | 1989 | Hollis, NH, USA | - |
| 08-09 | | Troy Maybury (F) | - | South Portland, ME, USA | - |
| 07-08 | | Ryan Mero (F) | 1985 | Peekskill, NY, USA | - |
| 06-07 | | Brendan O'Brien (F) | 1984 | Braintree, MA, USA | - |
| 05-06 | | Jared Silver (F) | 1984 | Montréal, QC, CAN | - |
| 04-05 | | Pat Doherty (F) | 1982 | Wakefield, MA, USA | - |
| 03-04 | | Rob Pascale (F) | 1982 | South Portland, ME, USA | - |
| 02-03 | | Rob Pascale (F) | 1982 | South Portland, ME, USA | - |
| 01-02 | | Michael Martiniello (F) | 1978 | Wilmington, MA, USA | - |
