[8] BOS Bruins 3-4 TOR Maple Leafs [12] 2019-10-19 23:00
Stadium: Scotiabank Arena
Home Manager: Mike Babcock Away Manager: Bruce Cassidy
Head to Head
| NHL | 2019/04/23 23:00 | TOR Maple Leafs v BOS Bruins | W | 1-5 |
| NHL | 2019/04/21 19:00 | BOS Bruins v TOR Maple Leafs | W | 4-2 |
| NHL | 2019/04/19 23:00 | TOR Maple Leafs v BOS Bruins | L | 2-1 |
| NHL | 2019/04/17 23:00 | BOS Bruins v TOR Maple Leafs | W | 6-4 |
| NHL | 2019/04/15 23:00 | BOS Bruins v TOR Maple Leafs | L | 2-3 |
| NHL | 2019/04/14 00:00 | TOR Maple Leafs v BOS Bruins | W | 1-4 |
| NHL | 2019/04/11 23:00 | TOR Maple Leafs v BOS Bruins | L | 4-1 |
| NHL | 2019/01/13 00:00 | BOS Bruins v TOR Maple Leafs | W | 3-2 |
Home History
| NHL | 2019/10/17 23:00 | TB Lightning v BOS Bruins | L | 4-3 |
| NHL | 2019/10/14 17:00 | ANA Ducks v BOS Bruins | W | 2-4 |
| NHL | 2019/10/12 23:00 | NJ Devils v BOS Bruins | W | 0-3 |
| NHL | 2019/10/11 01:00 | BOS Bruins v COL Avalanche | L | 2-4 |
| NHL | 2019/10/09 02:00 | BOS Bruins v VGS Golden Knights | W | 4-3 |
| NHL | 2019/10/06 01:00 | BOS Bruins v ARZ Coyotes | W | 1-0 |
| NHL | 2019/10/04 00:30 | BOS Bruins v DAL Stars | W | 2-1 |
| NHL Pre-Season | 2019/09/28 19:00 | CHI Blackhawks v BOS Bruins | W | 2-8 |
Away History
| NHL | 2019/10/16 23:00 | TOR Maple Leafs v WAS Capitals | L | 3-4 |
| NHL | 2019/10/15 23:00 | MIN Wild v TOR Maple Leafs | W | 2-4 |
| NHL | 2019/10/12 23:00 | TOR Maple Leafs v DET Red Wings | W | 5-2 |
| NHL | 2019/10/10 23:00 | TB Lightning v TOR Maple Leafs | L | 7-3 |
| NHL | 2019/10/07 23:00 | STL Blues v TOR Maple Leafs | L | 3-2 |
| NHL | 2019/10/05 23:00 | MON Canadiens v TOR Maple Leafs | L | 6-5 |
| 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 |