| Wins | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 2 | |  Jim Lorentz (F) | 1947 | Waterloo, ON, CAN | - |
| 2 | | Art Stratton (F) | 1935 | Winnipeg, MB, CAN | - |
| 2 | | Mike McMahon Jr. (D) | 1941 | Québec, QC, CAN | - |
| 1 | | Steve Atkinson (F) | 1948 | Toronto, ON, CAN | Detroit Red Wings (1966) |
| 1 | | Marv Edwards (G) | 1935 | St. Catharines, ON, CAN | - |
| 1 | | Barry Gibbs (D) | 1948 | Lloydminster, SK, CAN | Boston Bruins (1966) |
| 1 | | Gary Veneruzzo (F) | 1943 | Fort William, ON, CAN | - |
| 1 | | Barry Wilkins (D) | 1947 | Toronto, ON, CAN | - |
| 1 | | Ken Campbell (F) | 1943 | St. John's, NL, CAN | - |
| 1 | | Russ Gillow (G) | 1940 | Hespeler, ON, CAN | - |
| 1 | | Len Haley (F) | 1931 | Edmonton, AB, CAN | - |
| 1 | | Irv Spencer (D) | 1937 | Sudbury, ON, CAN | - |
| 1 | | Bryan Watson (D) | 1942 | Bancroft, ON, CAN | - |
| 1 | |  George Konik (D) | 1937 | Flin Flon, MB, CAN | - |
| 1 | | Larry Mickey (F) | 1943 | Lacombe, AB, CAN | - |
| 1 | | John Miszuk (D) | 1940 | Nalibaki, BLR | - |
| 1 | | Wayne Rutledge (G) | 1942 | Barrie, ON, CAN | - |
| 1 | | Marc Dufour (F) | 1941 | Trois-Rivières, QC, CAN | - |
| 1 | | Jean Gauthier (D) | 1937 | Montréal, QC, CAN | - |
| 1 | | Cesare Maniago (G) | 1939 | Trail, BC, CAN | - |
| 1 | | Tom McCarthy (F) | 1934 | Toronto, ON, CAN | - |
| 1 | | Mike Walton (F) | 1945 | Kirkland Lake, ON, CAN | - |
| 1 | | John Brenneman (F) | 1943 | Fort Erie, ON, CAN | - |
| 1 | | Alain Caron (F) | 1938 | Dolbeau, QC, CAN | - |
| 1 | | Ray Cullen (F) | 1941 | St. Catharines, ON, CAN | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 68-69 | | Marv Edwards (G) | 1935 | St. Catharines, ON, CAN | - |
| 68-69 | | Barry Gibbs (D) | 1948 | Lloydminster, SK, CAN | Boston Bruins (1966) |
| 68-69 | | Barry Wilkins (D) | 1947 | Toronto, ON, CAN | - |
| 68-69 | | Jim Lorentz (F) | 1947 | Waterloo, ON, CAN | - |
| 68-69 | | Gary Veneruzzo (F) | 1943 | Fort William, ON, CAN | - |
| 68-69 | | Steve Atkinson (F) | 1948 | Toronto, ON, CAN | Detroit Red Wings (1966) |
| 67-68 | | Russ Gillow (G) | 1940 | Hespeler, ON, CAN | - |
| 67-68 | | Irv Spencer (D) | 1937 | Sudbury, ON, CAN | - |
| 67-68 | | Bryan Watson (D) | 1942 | Bancroft, ON, CAN | - |
| 67-68 | | Jim Lorentz (F) | 1947 | Waterloo, ON, CAN | - |
| 67-68 | | Ken Campbell (F) | 1943 | St. John's, NL, CAN | - |
| 67-68 | | Len Haley (F) | 1931 | Edmonton, AB, CAN | - |
| 66-67 | | Wayne Rutledge (G) | 1942 | Barrie, ON, CAN | - |
| 66-67 | | George Konik (D) | 1937 | Flin Flon, MB, CAN | - |
| 66-67 | | Mike McMahon Jr. (D) | 1941 | Québec, QC, CAN | - |
| 66-67 | | John Miszuk (D) | 1940 | Nalibaki, BLR | - |
| 66-67 | | Art Stratton (F) | 1935 | Winnipeg, MB, CAN | - |
| 66-67 | | Larry Mickey (F) | 1943 | Lacombe, AB, CAN | - |
| 65-66 | | Art Stratton (F) | 1935 | Winnipeg, MB, CAN | - |
| 64-65 | | Cesare Maniago (G) | 1939 | Trail, BC, CAN | - |
| 64-65 | | Jean Gauthier (D) | 1937 | Montréal, QC, CAN | - |
| 64-65 | | Mike McMahon Jr. (D) | 1941 | Québec, QC, CAN | - |
| 64-65 | | Mike Walton (F) | 1945 | Kirkland Lake, ON, CAN | - |
| 64-65 | | Tom McCarthy (F) | 1934 | Toronto, ON, CAN | - |
| 64-65 | | Marc Dufour (F) | 1941 | Trois-Rivières, QC, CAN | - |
| 63-64 | | Marcel Pelletier (G) | 1927 | Sorel-Tracy, QC, CAN | - |
| 63-64 | | Barclay Plager (D) | 1941 | Kirkland Lake, ON, CAN | - |
| 63-64 | | Bob Woytowich (D) | 1941 | Winnipeg, MB, CAN | - |
| 63-64 | | Ray Cullen (F) | 1941 | St. Catharines, ON, CAN | - |
| 63-64 | | John Brenneman (F) | 1943 | Fort Erie, ON, CAN | - |
| 63-64 | | Bill McCreary (F) | 1934 | Sundridge, ON, CAN | - |
| 63-64 | | Alain Caron (F) | 1938 | Dolbeau, QC, CAN | - |