[15] MON Canadiens 6-5 TOR Maple Leafs [2] 2019-10-05 23:00
Stadium: Scotiabank Arena
Home Manager: Mike Babcock Away Manager: Claude Julien
Head to Head
| NHL Pre-Season | 2019/09/25 23:00 | MON Canadiens v TOR Maple Leafs | L | 0-3 |
| NHL Pre-Season | 2019/09/23 23:00 | TOR Maple Leafs v MON Canadiens | L | 3-0 |
| NHL | 2019/04/06 23:00 | TOR Maple Leafs v MON Canadiens | W | 5-6 |
| NHL | 2019/02/24 00:00 | MON Canadiens v TOR Maple Leafs | L | 3-6 |
| NHL | 2019/02/10 00:00 | TOR Maple Leafs v MON Canadiens | L | 4-3 |
| NHL | 2018/10/03 23:00 | MON Canadiens v TOR Maple Leafs | L | 2-3 |
| NHL Pre-Season | 2018/09/26 23:30 | TOR Maple Leafs v MON Canadiens | L | 5-3 |
| NHL Pre-Season | 2018/09/24 23:30 | MON Canadiens v TOR Maple Leafs | W | 5-1 |
| NHL | 2018/04/07 23:00 | MON Canadiens v TOR Maple Leafs | L | 2-4 |
| NHL | 2018/03/17 23:00 | MON Canadiens v TOR Maple Leafs | L | 0-4 |
| NHL | 2017/11/19 00:00 | TOR Maple Leafs v MON Canadiens | L | 6-0 |
| NHL | 2017/10/14 23:00 | TOR Maple Leafs v MON Canadiens | L | 4-3 |
| NHL Pre-Season | 2017/09/27 23:00 | TOR Maple Leafs v MON Canadiens | L | 4-2 |
| NHL Pre-Season | 2017/09/25 23:30 | MON Canadiens v TOR Maple Leafs | L | 1-5 |
| NHL | 2017/02/26 00:00 | MON Canadiens v TOR Maple Leafs | W | 3-2 |
| NHL | 2017/01/08 00:00 | MON Canadiens v TOR Maple Leafs | W | 5-3 |
| NHL | 2016/11/20 00:00 | TOR Maple Leafs v MON Canadiens | W | 1-2 |
| NHL | 2016/10/29 22:49 | TOR Maple Leafs v MON Canadiens | W | 1-2 |
| NHL Pre-Season | 2016/10/02 22:39 | MON Canadiens v TOR Maple Leafs | L | 2-3 |