[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 |
Home History
| NHL | 2019/10/03 23:00 | MON Canadiens v CAR Hurricanes | L | 3-4 |
| NHL Pre-Season | 2019/09/28 23:00 | OTT Senators v MON Canadiens | W | 3-4 |
| 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 Pre-Season | 2019/09/21 23:30 | MON Canadiens v OTT Senators | W | 4-0 |
| NHL Pre-Season | 2019/09/19 23:00 | FLA Panthers v MON Canadiens | W | 4-5 |
| NHL Pre-Season | 2019/09/18 23:00 | FLA Panthers v MON Canadiens | W | 3-4 |
| NHL Pre-Season | 2019/09/16 23:00 | MON Canadiens v NJ Devils | W | 4-2 |
Away History
| NHL | 2019/10/04 23:00 | TOR Maple Leafs v CLB Blue Jackets | W | 4-1 |
| NHL | 2019/10/02 23:00 | OTT Senators v TOR Maple Leafs | W | 3-5 |
| NHL Pre-Season | 2019/09/28 23:00 | DET Red Wings v TOR Maple Leafs | W | 0-5 |
| NHL Pre-Season | 2019/09/27 23:30 | TOR Maple Leafs v DET Red Wings | W | 4-3 |
| 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 |