| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Tyler Bilton (G) | 1983 | Penticton, BC, CAN | - |
| 1 | |  David Ciancio (D) | 2001 | Scituate, RI, USA | - |
| 1 | | Thomas McLarnon (G) | 1999 | Boyertown, PA, USA | - |
| 1 | | Nick Howard (G) | 1998 | Burlington, MA, USA | - |
| 1 | | Devan Sheth (F) | 1997 | Ashland, MA, USA | - |
| 1 | | Matt Schoen (G) | 1997 | Tolland, CT, USA | - |
| 1 | | Kurt Gutting (G) | 1996 | Weymouth, MA, USA | - |
| 1 | | Brenden Cain (G) | 1994 | Coppell, TX, USA | - |
| 1 | | Nick Commesso (G) | 1992 | Marshfield, MA, USA | - |
| 1 | | Johnny Daniels (F) | 1993 | Andover, MA, USA | - |
| 1 | | Tyler Holske (G) | 1991 | Attleboro, MA, USA | - |
| 1 | | Mike Richard (F) | 1989 | Derry, NH, USA | - |
| 1 | | Robert Kang (G) | 1991 | Glen Rock, NJ, USA | - |
| 1 | | Nick Wheeler (D) | 1988 | Glendale, AZ, USA | - |
| 1 | | Coleman Noonan (F) | 1989 | Norfolk, MA, USA | - |
| 1 | | James Florentino (D) | 1987 | West Roxbury, MA, USA | - |
| 1 | | Josh Hechter (F) | 1982 | Winnipeg, MB, CAN | - |
| 1 | | John Cronin (F) | - | Milton, MA, USA | - |
| 1 | | Jared Silver (F) | 1984 | Montréal, QC, CAN | - |
| 1 | | Alex Watts (F) | - | Cheshire, CT, USA | - |
| 1 | | Nick Berno (F) | - | Rochester, NY, USA | - |
| 1 | | Ted McNaught (F) | 1978 | Gorham, ME, USA | - |
| 1 | | Nick Solis (F) | - | Tewksbury, MA, USA | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 24-25 | | David Ciancio (D) | 2001 | Scituate, RI, USA | - |
| 23-24 | | Thomas McLarnon (G) | 1999 | Boyertown, PA, USA | - |
| 22-23 | | Nick Howard (G) | 1998 | Burlington, MA, USA | - |
| 21-22 | | Devan Sheth (F) | 1997 | Ashland, MA, USA | - |
| 19-20 | | Matt Schoen (G) | 1997 | Tolland, CT, USA | - |
| 18-19 | | Kurt Gutting (G) | 1996 | Weymouth, MA, USA | - |
| 17-18 | | Brenden Cain (G) | 1994 | Coppell, TX, USA | - |
| 16-17 | | Nick Commesso (G) | 1992 | Marshfield, MA, USA | - |
| 14-15 | | Johnny Daniels (F) | 1993 | Andover, MA, USA | - |
| 13-14 | | Tyler Holske (G) | 1991 | Attleboro, MA, USA | - |
| 12-13 | | Mike Richard (F) | 1989 | Derry, NH, USA | - |
| 11-12 | | Robert Kang (G) | 1991 | Glen Rock, NJ, USA | - |
| 10-11 | | Nick Wheeler (D) | 1988 | Glendale, AZ, USA | - |
| 09-10 | | Coleman Noonan (F) | 1989 | Norfolk, MA, USA | - |
| 08-09 | | Tyler Bilton (G) | 1983 | Penticton, BC, CAN | - |
| 07-08 | | Tyler Bilton (G) | 1983 | Penticton, BC, CAN | - |
| 06-07 | | James Florentino (D) | 1987 | West Roxbury, MA, USA | - |
| 05-06 | | Josh Hechter (F) | 1982 | Winnipeg, MB, CAN | - |
| 04-05 | | John Cronin (F) | - | Milton, MA, USA | - |
| 03-04 | | Jared Silver (F) | 1984 | Montréal, QC, CAN | - |
| 02-03 | | Alex Watts (F) | - | Cheshire, CT, USA | - |
| 01-02 | | Nick Berno (F) | - | Rochester, NY, USA | - |
| 00-01 | | Ted McNaught (F) | 1978 | Gorham, ME, USA | - |
| 99-00 | | Nick Solis (F) | - | Tewksbury, MA, USA | - |
