TOR Maple Leafs 4-3 DET Red Wings 2019-09-27 23:30
Stadium: Little Caesars Arena
Home Manager: Jeff Blashill Away Manager: Mike Babcock
Head to Head
| NHL | 2019/02/02 00:30 | TOR Maple Leafs v DET Red Wings | L | 2-3 |
| NHL | 2018/12/24 00:30 | DET Red Wings v TOR Maple Leafs | W | 4-5 |
| NHL | 2018/12/07 00:00 | DET Red Wings v TOR Maple Leafs | L | 5-4 |
| NHL | 2018/10/11 23:30 | TOR Maple Leafs v DET Red Wings | W | 5-3 |
| NHL Pre-Season | 2018/09/29 23:05 | TOR Maple Leafs v DET Red Wings | L | 1-5 |
| NHL Pre-Season | 2018/09/29 23:00 | DET Red Wings v TOR Maple Leafs | L | 5-1 |
| NHL Pre-Season | 2018/09/28 23:30 | DET Red Wings v TOR Maple Leafs | W | 2-6 |
| NHL | 2018/03/24 23:00 | DET Red Wings v TOR Maple Leafs | W | 3-4 |
Home History
| NHL Pre-Season | 2019/09/25 23:00 | MON Canadiens v TOR Maple Leafs | W | 0-3 |
| NHL Pre-Season | 2019/09/23 23:00 | TOR Maple Leafs v MON Canadiens | W | 3-0 |
| NHL Pre-Season | 2019/09/21 23:00 | TOR Maple Leafs v BUF Sabres | L | 3-5 |
| NHL Pre-Season | 2019/09/20 23:00 | BUF Sabres v TOR Maple Leafs | W | 0-3 |
| NHL Pre-Season | 2019/09/18 23:30 | TOR Maple Leafs v OTT Senators | L | 3-4 |
| NHL Pre-Season | 2019/09/17 21:30 | OTT Senators v TOR Maple Leafs | L | 3-1 |
| NHL | 2019/04/23 23:00 | TOR Maple Leafs v BOS Bruins | L | 1-5 |
| NHL | 2019/04/21 19:00 | BOS Bruins v TOR Maple Leafs | L | 4-2 |
Away History
| NHL Pre-Season | 2019/09/26 23:00 | STL Blues v DET Red Wings | W | 1-4 |
| NHL Pre-Season | 2019/09/25 23:00 | DET Red Wings v PIT Penguins | L | 2-4 |
| NHL Pre-Season | 2019/09/23 23:00 | DET Red Wings v NY Islanders | L | 2-3 |
| NHL Pre-Season | 2019/09/22 21:00 | PIT Penguins v DET Red Wings | W | 2-3 |
| NHL Pre-Season | 2019/09/20 23:30 | NY Islanders v DET Red Wings | L | 4-3 |
| NHL Pre-Season | 2019/09/19 00:30 | DET Red Wings v CHI Blackhawks | L | 1-2 |
| NHL Pre-Season | 2019/09/17 23:30 | CHI Blackhawks v DET Red Wings | W | 3-5 |
| NHL | 2019/04/06 23:00 | BUF Sabres v DET Red Wings | L | 7-1 |