| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Ladysmith | 26 | Cumberland | 56 | |
| 8/30/2019 | 2 | Saint Croix Falls | 18 | Cumberland | 20 | |
| 9/6/2019 | 3 | Cumberland | 50 | Barron | 1 | |
| 9/13/2019 | 4 | Northwestern | 37 | Cumberland | 6 | |
| 9/20/2019 | 5 | Cumberland | 58 | Cameron | 6 | |
| 9/27/2019 | 6 | Bloomer | 28 | Cumberland | 34 | 1OT |
| 10/4/2019 | 7 | Cumberland | 46 | Chetek-Weyerhaeuser | 12 | |
| 10/11/2019 | 8 | Spooner | 18 | Cumberland | 22 | |
| 10/18/2019 | 9 | Cumberland | 24 | Hayward/La Courte Oreilles | 0 | |