Awards - NHL Stanley Cup Champion (As General Manager)
Most Award Wins (Players)
| Wins | Award Winner | Born | Birthplace | Drafted By | |
|---|---|---|---|---|---|
| 3 |  Ken Holland (G) | 1955 | Vernon, BC, CAN | Toronto Maple Leafs (1975) |
1 player
All Winners (Players)
| S | Award Winner | Born | Birthplace | Drafted By | |
|---|---|---|---|---|---|
| 07-08 | Ken Holland (G) | 1955 | Vernon, BC, CAN | Toronto Maple Leafs (1975) | |
| 01-02 | Ken Holland (G) | 1955 | Vernon, BC, CAN | Toronto Maple Leafs (1975) | |
| 97-98 | Ken Holland (G) | 1955 | Vernon, BC, CAN | Toronto Maple Leafs (1975) |
3 players