| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Zac McCann (F) | 2002 | Stratford, ON, CAN | - |
| 2 | | Holdyn Lansink (F) | 1998 | Clinton, ON, CAN | - |
| 2 | | Ethan Skinner (F) | 1997 | Kincardine, ON, CAN | - |
| 2 | | Logan Schmidt (D) | 1996 | Kitchener, ON, CAN | - |
| 1 | | Riley Arts (G) | 2005 | Innisfil, ON, CAN | - |
| 1 | | Jake DaSilva (F) | 2003 | Cambridge, ON, CAN | - |
| 1 | | Luke Eurig (F) | 2003 | Mount Forest, ON, CAN | - |
| 1 | | Liam Eveleigh (D) | 2004 | Elmira, ON, CAN | - |
| 1 | | Matthew Fries (F) | 2004 | Cambridge, ON, CAN | - |
| 1 | | Riley Noble (D) | 2004 | Waterloo, ON, CAN | - |
| 1 | | Tanner Bibby (F) | 2002 | Brantford, ON, CAN | - |
| 1 | | Nolan Chartrand (G) | 2004 | Kitchener, ON, CAN | - |
| 1 | | Reid Oliver (D) | 2002 | Elmira, ON, CAN | - |
| 1 | |  Andrew Van Antwerp (D) | 2003 | Petoskey, MI, USA | - |
| 1 | | Blake Wideman (F) | 2002 | Mildmay, ON, CAN | - |
| 1 | | Daniel Botelho (G) | 2002 | Nottawa, ON, CAN | - |
| 1 | | Jacob Coulson (F) | 2001 | Caledon, ON, CAN | - |
| 1 | | Brody LeBlanc (F) | 2002 | Mount Forest, ON, CAN | - |
| 1 | | Nathaniel Mott (D) | 2001 | Mississauga, ON, CAN | - |
| 1 | | Derek Pys (D) | 2002 | Ayr, ON, CAN | - |
| 1 | | Brenden Clayton (D) | 1999 | Hanover, ON, CAN | - |
| 1 | | Jeremy Goodwin (F) | 1999 | Fergus, ON, CAN | - |
| 1 | | Sean Kawalec (F) | 2000 | Kitchener, ON, CAN | - |
| 1 | | Alex Peterson (D) | 1999 | Kenora, ON, CAN | - |
| 1 | | Owen Porter (G) | 2001 | Brampton, ON, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 23-24 | | Riley Arts (G) | 2005 | Innisfil, ON, CAN | - |
| 23-24 | | Liam Eveleigh (D) | 2004 | Elmira, ON, CAN | - |
| 23-24 | | Riley Noble (D) | 2004 | Waterloo, ON, CAN | - |
| 23-24 | | Jake DaSilva (F) | 2003 | Cambridge, ON, CAN | - |
| 23-24 | | Matthew Fries (F) | 2004 | Cambridge, ON, CAN | - |
| 23-24 | | Luke Eurig (F) | 2003 | Mount Forest, ON, CAN | - |
| 22-23 | | Nolan Chartrand (G) | 2004 | Kitchener, ON, CAN | - |
| 22-23 | | Reid Oliver (D) | 2002 | Elmira, ON, CAN | - |
| 22-23 | | Andrew Van Antwerp (D) | 2003 | Petoskey, MI, USA | - |
| 22-23 | | Zac McCann (F) | 2002 | Stratford, ON, CAN | - |
| 22-23 | | Tanner Bibby (F) | 2002 | Brantford, ON, CAN | - |
| 22-23 | | Blake Wideman (F) | 2002 | Mildmay, ON, CAN | - |
| 21-22 | | Daniel Botelho (G) | 2002 | Nottawa, ON, CAN | - |
| 21-22 | | Nathaniel Mott (D) | 2001 | Mississauga, ON, CAN | - |
| 21-22 | | Derek Pys (D) | 2002 | Ayr, ON, CAN | - |
| 21-22 | | Jacob Coulson (F) | 2001 | Caledon, ON, CAN | - |
| 21-22 | | Zac McCann (F) | 2002 | Stratford, ON, CAN | - |
| 21-22 | | Brody LeBlanc (F) | 2002 | Mount Forest, ON, CAN | - |
| 19-20 | | Owen Porter (G) | 2001 | Brampton, ON, CAN | - |
| 19-20 | | Brenden Clayton (D) | 1999 | Hanover, ON, CAN | - |
| 19-20 | | Alex Peterson (D) | 1999 | Kenora, ON, CAN | - |
| 19-20 | | Drew Welsch (F) | 2000 | Trenton, MI, USA | - |
| 19-20 | | Jeremy Goodwin (F) | 1999 | Fergus, ON, CAN | - |
| 19-20 | | Sean Kawalec (F) | 2000 | Kitchener, ON, CAN | - |
| 18-19 | | Zack Weir (G) | 1998 | London, ON, CAN | - |
| 18-19 | | Mark Cooper (D) | 2001 | Cambridge, ON, CAN | - |
| 18-19 | | Tyler Dam (D) | 1999 | Kitchener, ON, CAN | - |
| 18-19 | | Sean Ross (F) | 1998 | Bracebridge, ON, CAN | - |
| 18-19 | | Chayse Herrfort (F) | 1998 | Minto, ON, CAN | - |
| 18-19 | | Holdyn Lansink (F) | 1998 | Clinton, ON, CAN | - |
| 17-18 | | Max Wright (G) | 1999 | Waterloo, ON, CAN | - |
| 17-18 | | Max Coyle (D) | 1998 | Tillsonburg, ON, CAN | - |
| 17-18 | | Ryan Nicholson (D) | 1999 | Mississauga, ON, CAN | - |
| 17-18 | | Cullen Mercer (F) | 1997 | Exeter, ON, CAN | - |
| 17-18 | | Ethan Skinner (F) | 1997 | Kincardine, ON, CAN | - |
| 17-18 | | Jack Scanlan (F) | 1997 | Penetanguishene, ON, CAN | - |
| 16-17 | | Jonathan Reinhart (G) | 1996 | Cambridge, ON, CAN | - |
| 16-17 | | Jordan Oshowy (D) | 1996 | Woodbridge, ON, CAN | - |
| 16-17 | | Logan Schmidt (D) | 1996 | Kitchener, ON, CAN | - |
| 16-17 | | Connor Cole (F) | 1996 | Kitchener, ON, CAN | - |
| 16-17 | | Ethan Skinner (F) | 1997 | Kincardine, ON, CAN | - |
| 16-17 | | Holdyn Lansink (F) | 1998 | Clinton, ON, CAN | - |
| 15-16 | | Luke Richardson (G) | 1999 | Barrie, ON, CAN | - |
| 15-16 | | Joe Leahy (D) | 1997 | Waterloo, ON, CAN | - |
| 15-16 | | Logan Schmidt (D) | 1996 | Kitchener, ON, CAN | - |
| 15-16 | | Adam Kawalec (F) | 1996 | Kitchener, ON, CAN | - |
| 15-16 | | Nate Schnarr (F) | 1999 | Waterloo, ON, CAN | Arizona Coyotes (2017) |
| 15-16 | | Hayden Broomhead (F) | 1997 | Ilderton, ON, CAN | - |
| 13-14 | | Marc Williams (G) | 1994 | Waterloo, ON, CAN | - |
| 13-14 | | Ryker Killins (D) | 1996 | Wawa, ON, CAN | - |
| 13-14 | | Mackenzie Nichol (D) | 1993 | Listowel, ON, CAN | - |
| 13-14 | | Adam Campagnolo (F) | 1993 | Waterloo, ON, CAN | - |
| 13-14 | | Keli Grant (F) | 1993 | Kingston, ON, CAN | - |
| 13-14 | | Matt Lippa (F) | 1994 | Richmond Hill, ON, CAN | - |
