[31] DET Red Wings 1-4 TOR Maple Leafs [17] 2019-12-22 00:00
Stadium: Scotiabank Arena
Home Manager: Sheldon Keefe Away Manager: Jeff Blashill
Head to Head
| NHL | 2019/11/28 00:00 | TOR Maple Leafs v DET Red Wings | L | 6-0 |
| NHL | 2019/10/12 23:00 | TOR Maple Leafs v DET Red Wings | L | 5-2 |
| NHL Pre-Season | 2019/09/28 23:00 | DET Red Wings v TOR Maple Leafs | L | 0-5 |
| NHL Pre-Season | 2019/09/27 23:30 | TOR Maple Leafs v DET Red Wings | L | 4-3 |
| NHL | 2019/02/02 00:30 | TOR Maple Leafs v DET Red Wings | W | 2-3 |
| NHL | 2018/12/24 00:30 | DET Red Wings v TOR Maple Leafs | L | 4-5 |
| NHL | 2018/12/07 00:00 | DET Red Wings v TOR Maple Leafs | W | 5-4 |
| NHL | 2018/10/11 23:30 | TOR Maple Leafs v DET Red Wings | L | 5-3 |
Home History
| NHL | 2019/12/18 00:30 | CLB Blue Jackets v DET Red Wings | L | 5-3 |
| NHL | 2019/12/16 00:00 | LA Kings v DET Red Wings | L | 4-2 |
| NHL | 2019/12/15 00:00 | DET Red Wings v MON Canadiens | W | 2-1 |
| NHL | 2019/12/13 00:30 | WIN Jets v DET Red Wings | W | 2-5 |
| NHL | 2019/12/11 01:00 | DET Red Wings v WIN Jets | L | 1-5 |
| NHL | 2019/12/08 00:00 | PIT Penguins v DET Red Wings | L | 5-3 |
| NHL | 2019/12/03 00:30 | NY Islanders v DET Red Wings | L | 4-1 |
| NHL | 2019/12/01 00:00 | WAS Capitals v DET Red Wings | L | 5-2 |
Away History
| NHL | 2019/12/21 00:00 | TOR Maple Leafs v NY Rangers | W | 6-3 |
| NHL | 2019/12/18 00:00 | BUF Sabres v TOR Maple Leafs | W | 3-5 |
| NHL | 2019/12/15 00:00 | TOR Maple Leafs v EDM Oilers | W | 4-1 |
| NHL | 2019/12/13 02:00 | TOR Maple Leafs v CAL Flames | L | 2-4 |
| NHL | 2019/12/11 03:00 | TOR Maple Leafs v VAN Canucks | W | 4-1 |
| NHL | 2019/12/08 00:00 | TOR Maple Leafs v STL Blues | W | 5-2 |
| NHL | 2019/12/05 00:00 | COL Avalanche v TOR Maple Leafs | L | 3-1 |
| NHL | 2019/12/04 00:00 | TOR Maple Leafs v PHI Flyers | L | 1-6 |