[5] BOS Bruins 4-2 TOR Maple Leafs [17] 2019-11-16 00:00
Estadio: Scotiabank Arena
Home Manager: Mike Babcock Away Manager: Bruce Cassidy
Head to Head
| NHL | 2019/10/22 23:00 | TOR Maple Leafs v BOS Bruins | W | 2-4 |
| NHL | 2019/10/19 23:00 | BOS Bruins v TOR Maple Leafs | L | 3-4 |
| 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 |
Home History
| NHL | 2019/11/13 00:00 | FLA Panthers v BOS Bruins | L | 5-4 |
| NHL | 2019/11/11 00:00 | PHI Flyers v BOS Bruins | L | 3-2 |
| NHL | 2019/11/09 00:30 | BOS Bruins v DET Red Wings | L | 2-4 |
| NHL | 2019/11/06 00:30 | BOS Bruins v MON Canadiens | L | 4-5 |
| NHL | 2019/11/05 00:00 | PIT Penguins v BOS Bruins | W | 4-6 |
| NHL | 2019/11/02 23:00 | OTT Senators v BOS Bruins | W | 2-5 |
| NHL | 2019/10/29 23:00 | SJ Sharks v BOS Bruins | W | 1-5 |
| NHL | 2019/10/27 23:00 | BOS Bruins v NY Rangers | W | 7-4 |
Away History
| NHL | 2019/11/14 00:00 | TOR Maple Leafs v NY Islanders | L | 4-5 |
| NHL | 2019/11/11 00:00 | TOR Maple Leafs v CHI Blackhawks | L | 4-5 |
| NHL | 2019/11/10 00:00 | PHI Flyers v TOR Maple Leafs | L | 3-2 |
| NHL | 2019/11/08 00:00 | VGS Golden Knights v TOR Maple Leafs | W | 1-2 |
| NHL | 2019/11/06 00:30 | LA Kings v TOR Maple Leafs | W | 1-3 |
| NHL | 2019/11/02 23:00 | TOR Maple Leafs v PHI Flyers | W | 4-3 |
| NHL | 2019/10/29 23:00 | WAS Capitals v TOR Maple Leafs | L | 4-3 |
| NHL | 2019/10/26 23:00 | TOR Maple Leafs v MON Canadiens | L | 2-5 |