[5] NY Islanders 3-2 BOS Bruins [3] 2019-12-20 00:00
Stadium: TD Garden
Home Manager: Bruce Cassidy Away Manager: Barry Trotz
Head to Head
| NHL | 2019/03/19 23:00 | BOS Bruins v NY Islanders | L | 5-0 |
| NHL | 2019/02/06 00:00 | NY Islanders v BOS Bruins | L | 1-3 |
| NHL | 2018/11/30 00:00 | NY Islanders v BOS Bruins | L | 1-2 |
| NHL | 2018/01/19 00:00 | BOS Bruins v NY Islanders | L | 5-2 |
| NHL | 2018/01/03 00:00 | BOS Bruins v NY Islanders | L | 5-1 |
| NHL | 2017/12/10 00:00 | NY Islanders v BOS Bruins | L | 1-3 |
| NHL | 2017/03/25 23:00 | BOS Bruins v NY Islanders | L | 2-1 |
| NHL | 2017/01/16 18:00 | NY Islanders v BOS Bruins | W | 4-0 |
Home History
| NHL | 2019/12/18 00:00 | NAS Predators v NY Islanders | L | 8-3 |
| NHL | 2019/12/14 18:00 | BUF Sabres v NY Islanders | W | 2-3 |
| NHL | 2019/12/13 00:00 | NY Islanders v FLA Panthers | W | 3-1 |
| NHL | 2019/12/10 00:00 | NY Islanders v TB Lightning | W | 5-1 |
| NHL | 2019/12/08 02:00 | NY Islanders v DAL Stars | L | 1-3 |
| NHL | 2019/12/06 00:00 | VGS Golden Knights v NY Islanders | W | 2-3 |
| NHL | 2019/12/04 00:00 | NY Islanders v MON Canadiens | L | 2-4 |
| NHL | 2019/12/03 00:30 | NY Islanders v DET Red Wings | W | 4-1 |
Away History
| NHL | 2019/12/18 00:00 | LA Kings v BOS Bruins | L | 4-3 |
| NHL | 2019/12/15 00:00 | BOS Bruins v FLA Panthers | W | 4-2 |
| NHL | 2019/12/13 00:00 | BOS Bruins v TB Lightning | L | 2-3 |
| NHL | 2019/12/12 00:00 | BOS Bruins v WAS Capitals | L | 2-3 |
| NHL | 2019/12/10 00:30 | BOS Bruins v OTT Senators | L | 2-5 |
| NHL | 2019/12/08 00:00 | COL Avalanche v BOS Bruins | L | 4-1 |
| NHL | 2019/12/06 00:00 | CHI Blackhawks v BOS Bruins | L | 4-3 |
| NHL | 2019/12/04 00:00 | CAR Hurricanes v BOS Bruins | W | 0-2 |