| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Jeff Lupu (F) | 1971 | Royal Oak, MI, USA | - |
| 1 | |  Brandon Cohen (F) | 2003 | Toronto, ON, CAN | - |
| 1 | | Anthony Bernardo (F) | 2000 | Hauppauge, NY, USA | - |
| 1 | | Eli Shiller (G) | 2001 | Toronto, ON, CAN | - |
| 1 | | Danny Bosio (F) | 1996 | Brighton, MI, USA | - |
| 1 | | Aaron MacKay (G) | 1997 | Okotoks, AB, CAN | - |
| 1 | | Mitch Ferguson (D) | 1994 | Calgary, AB, CAN | - |
| 1 | | David Szmyd (F) | 1995 | Elmwood Park, NJ, USA | - |
| 1 | | Brady Rouleau (G) | 1993 | Lethbridge, AB, CAN | - |
| 1 | | Stephen Collins (F) | 1991 | Rochester, NY, USA | - |
| 1 | | Connor Toomey (F) | 1990 | Billerica, MA, USA | - |
| 1 | | Alex Botten (F) | 1992 | Sharon, ON, CAN | - |
| 1 | | Andrew Hare (G) | 1990 | Peterborough, ON, CAN | - |
| 1 | | Josh Leis (G) | 1988 | Kitchener, ON, CAN | - |
| 1 | | Kevin Huinink (D) | 1987 | Whitby, ON, CAN | - |
| 1 | | Riley Hill (F) | 1987 | Markham, ON, CAN | - |
| 1 | | Bryan Hince (G) | 1986 | Kapuskasing, ON, CAN | - |
| 1 | | Kevin Amborski (G) | 1983 | Bloomfield, NY, USA | - |
| 1 | | Mitch Stephens (F) | 1982 | Forrest, MB, CAN | - |
| 1 | | Brett Walker (G) | 1980 | Regina, SK, CAN | - |
| 1 | | Chad Kemp (D) | 1979 | Strathroy, ON, CAN | - |
| 1 | | Mike Lukajic (F) | 1981 | Mississauga, ON, CAN | - |
| 1 | | Jeff Marshall (D) | 1978 | Newmarket, ON, CAN | - |
| 1 | | Derrick Shaw (F) | 1976 | Scottsdale, AZ, USA | - |
| 1 | | Paul Dowe (F) | 1979 | East Windsor, CT, USA | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 24-25 | | Brandon Cohen (F) | 2003 | Toronto, ON, CAN | - |
| 23-24 | | Anthony Bernardo (F) | 2000 | Hauppauge, NY, USA | - |
| 22-23 | | Eli Shiller (G) | 2001 | Toronto, ON, CAN | - |
| 21-22 | | Danny Bosio (F) | 1996 | Brighton, MI, USA | - |
| 19-20 | | Aaron MacKay (G) | 1997 | Okotoks, AB, CAN | - |
| 18-19 | | Mitch Ferguson (D) | 1994 | Calgary, AB, CAN | - |
| 17-18 | | David Szmyd (F) | 1995 | Elmwood Park, NJ, USA | - |
| 16-17 | | Brady Rouleau (G) | 1993 | Lethbridge, AB, CAN | - |
| 15-16 | | Stephen Collins (F) | 1991 | Rochester, NY, USA | - |
| 14-15 | | Connor Toomey (F) | 1990 | Billerica, MA, USA | - |
| 13-14 | | Alex Botten (F) | 1992 | Sharon, ON, CAN | - |
| 12-13 | | Andrew Hare (G) | 1990 | Peterborough, ON, CAN | - |
| 10-11 | | Josh Leis (G) | 1988 | Kitchener, ON, CAN | - |
| 09-10 | | Kevin Huinink (D) | 1987 | Whitby, ON, CAN | - |
| 08-09 | | Riley Hill (F) | 1987 | Markham, ON, CAN | - |
| 07-08 | | Bryan Hince (G) | 1986 | Kapuskasing, ON, CAN | - |
| 06-07 | | Kevin Amborski (G) | 1983 | Bloomfield, NY, USA | - |
| 05-06 | | Mitch Stephens (F) | 1982 | Forrest, MB, CAN | - |
| 04-05 | | Brett Walker (G) | 1980 | Regina, SK, CAN | - |
| 03-04 | | Chad Kemp (D) | 1979 | Strathroy, ON, CAN | - |
| 02-03 | | Mike Lukajic (F) | 1981 | Mississauga, ON, CAN | - |
| 01-02 | | Jeff Marshall (D) | 1978 | Newmarket, ON, CAN | - |
| 00-01 | | Derrick Shaw (F) | 1976 | Scottsdale, AZ, USA | - |
| 99-00 | | Paul Dowe (F) | 1979 | East Windsor, CT, USA | - |
| 98-99 | | Tracey Belanger (F) | 1979 | Merrimack, NH, USA | - |
| 97-98 | | Eric Weidenbach (F) | 1976 | Clarkston, MI, USA | - |
| 96-97 | | Steve Moffatt (F) | 1973 | Hatboro, PA, USA | - |
| 95-96 | | Tony Matczynski (F) | - | Richfield, MN, USA | - |
| 94-95 | | Jeff Lupu (F) | 1971 | Royal Oak, MI, USA | - |
| 93-94 | | Jeff Lupu (F) | 1971 | Royal Oak, MI, USA | - |
| 92-93 | | Steve Moore (F) | 1971 | Gardiner, ME, USA | - |
