[10] MON Canadiens 3-6 Kalmar FF U19 [8] 2019-01-28 08:00
Stadium: Scotiabank Arena Round: 1
Home Manager: Mike Babcock Away Manager: Claude Julien
Head to Head
| NHL | 2018/10/03 23:00 | MTL Canadiens v TOR Maple Leafs | L | 2-3 |
| NHL Pre-Season | 2018/09/26 23:30 | TOR Maple Leafs v MTL Canadiens | L | 5-3 |
| NHL Pre-Season | 2018/09/24 23:30 | MTL Canadiens v TOR Maple Leafs | W | 5-1 |
| NHL | 2018/04/07 23:00 | MTL Canadiens v TOR Maple Leafs | L | 2-4 |
| NHL | 2018/03/17 23:00 | MTL Canadiens v TOR Maple Leafs | L | 0-4 |
| NHL | 2017/11/19 00:00 | TOR Maple Leafs v MTL Canadiens | L | 6-0 |
| NHL | 2017/10/14 23:00 | TOR Maple Leafs v MTL Canadiens | L | 4-3 |
| NHL Pre-Season | 2017/09/27 23:00 | TOR Maple Leafs v MTL Canadiens | L | 4-2 |
Home History
| NHL | 2019/01/24 00:30 | ARZ Coyotes v MTL Canadiens | W | 1-2 |
| NHL | 2019/01/20 00:00 | PHI Flyers v MTL Canadiens | L | 5-2 |
| NHL | 2019/01/19 00:00 | MTL Canadiens v CLB Blue Jackets | W | 4-1 |
| NHL | 2019/01/16 00:30 | FLA Panthers v MTL Canadiens | W | 1-5 |
| NHL | 2019/01/15 00:30 | MTL Canadiens v BOS Bruins | W | 3-2 |
| NHL | 2019/01/13 00:00 | COL Avalanche v MTL Canadiens | W | 0-3 |
| NHL | 2019/01/11 01:00 | MTL Canadiens v STL Blues | L | 1-4 |
| NHL | 2019/01/09 00:30 | MTL Canadiens v DET Red Wings | W | 3-2 |
Away History
| NHL | 2019/01/24 00:30 | WAS Capitals v TOR Maple Leafs | W | 3-6 |
| NHL | 2019/01/21 00:00 | ARZ Coyotes v TOR Maple Leafs | L | 4-2 |
| NHL | 2019/01/19 00:00 | TOR Maple Leafs v FLA Panthers | L | 1-3 |
| NHL | 2019/01/18 00:30 | TOR Maple Leafs v TB Lightning | W | 4-2 |
| NHL | 2019/01/15 00:00 | COL Avalanche v TOR Maple Leafs | L | 6-3 |
| NHL | 2019/01/13 00:00 | BOS Bruins v TOR Maple Leafs | L | 3-2 |
| NHL | 2019/01/11 00:00 | TOR Maple Leafs v NJ Devils | W | 4-2 |
| NHL | 2019/01/08 00:00 | NSH Predators v TOR Maple Leafs | L | 4-0 |