DET Red Wings 0-5 TOR Maple Leafs 2019-09-28 23:00
Stadium: Scotiabank Arena
Home Manager: Mike Babcock Away Manager: Jeff Blashill
Head to Head
| 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 |
| NHL Pre-Season | 2018/09/29 23:05 | TOR Maple Leafs v DET Red Wings | W | 1-5 |
| NHL Pre-Season | 2018/09/29 23:00 | DET Red Wings v TOR Maple Leafs | W | 5-1 |
| NHL Pre-Season | 2018/09/28 23:30 | DET Red Wings v TOR Maple Leafs | L | 2-6 |
| NHL | 2018/03/24 23:00 | DET Red Wings v TOR Maple Leafs | L | 3-4 |
| NHL | 2018/02/19 00:00 | TOR Maple Leafs v DET Red Wings | L | 3-2 |
| NHL | 2017/12/16 00:30 | TOR Maple Leafs v DET Red Wings | W | 1-3 |
| NHL | 2017/10/18 23:30 | DET Red Wings v TOR Maple Leafs | L | 3-6 |
| NHL Pre-Season | 2017/09/30 23:00 | DET Red Wings v TOR Maple Leafs | W | 3-2 |
| NHL Pre-Season | 2017/09/29 23:30 | TOR Maple Leafs v DET Red Wings | L | 4-2 |
| NHL | 2017/04/01 23:00 | TOR Maple Leafs v DET Red Wings | L | 5-4 |
| NHL | 2017/03/08 00:30 | DET Red Wings v TOR Maple Leafs | L | 2-3 |
| NHL | 2017/01/26 00:00 | TOR Maple Leafs v DET Red Wings | L | 4-0 |
| NHL | 2017/01/01 20:30 | DET Red Wings v TOR Maple Leafs | L | 4-5 |
| NHL Pre-Season | 2016/10/08 22:56 | TOR Maple Leafs v DET Red Wings | W | 0-2 |
| NHL Pre-Season | 2016/10/07 22:54 | DET Red Wings v TOR Maple Leafs | W | 2-1 |