Stadium: PPG Paints Arena Round: 1
Home Manager: Jeff Blashill Away Manager: Mike Sullivan
| NHL Pre-Season | 2018/09/23 19:00 | DET Red Wings v PIT Penguins | W | 3-2 |
| NHL Pre-Season | 2018/09/19 23:30 | PIT Penguins v DET Red Wings | W | 2-3 |
| NHL | 2018/03/27 23:30 | PIT Penguins v DET Red Wings | W | 2-5 |
| NHL | 2018/01/13 18:00 | DET Red Wings v PIT Penguins | L | 1-4 |
| NHL | 2018/01/01 00:00 | PIT Penguins v DET Red Wings | W | 1-4 |
| NHL Pre-Season | 2017/09/25 23:30 | PIT Penguins v DET Red Wings | W | 1-4 |
| NHL Pre-Season | 2017/09/20 23:00 | PIT Penguins v DET Red Wings | L | 6-5 |
| NHL | 2017/02/19 21:30 | DET Red Wings v PIT Penguins | W | 5-2 |
| NHL | 2018/12/07 00:00 | DET Red Wings v TOR Maple Leafs | W | 5-4 |
| NHL | 2018/12/05 00:30 | TB Lightning v DET Red Wings | L | 6-5 |
| NHL | 2018/12/03 00:00 | COL Avalanche v DET Red Wings | L | 2-0 |
| NHL | 2018/12/02 00:00 | DET Red Wings v BOS Bruins | W | 4-2 |
| NHL | 2018/11/29 00:00 | STL Blues v DET Red Wings | W | 3-4 |
| NHL | 2018/11/27 00:30 | CLB Blue Jackets v DET Red Wings | L | 7-5 |
| NHL | 2018/11/25 00:00 | BUF Sabres v DET Red Wings | L | 3-2 |
| NHL | 2018/11/23 21:00 | DET Red Wings v WAS Capitals | L | 1-3 |
| NHL | 2018/12/07 00:00 | NY Islanders v PIT Penguins | W | 2-6 |
| NHL | 2018/12/05 00:00 | COL Avalanche v PIT Penguins | W | 3-6 |
| NHL | 2018/12/02 00:00 | PHI Flyers v PIT Penguins | L | 4-2 |
| NHL | 2018/11/29 02:30 | PIT Penguins v COL Avalanche | L | 3-6 |
| NHL | 2018/11/28 01:00 | PIT Penguins v WPG Jets | W | 4-3 |
| NHL | 2018/11/25 00:00 | CLB Blue Jackets v PIT Penguins | W | 2-4 |
| NHL | 2018/11/24 00:30 | PIT Penguins v BOS Bruins | L | 1-2 |
| NHL | 2018/11/22 00:00 | DAL Stars v PIT Penguins | W | 1-5 |