| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Hayward/Lac Courte Oreilles (NC) | 21 | Cumberland | 14 | |
| 8/25/2023 | 2 | Cumberland | 9 | Ladysmith (NC) | 29 | |
| 9/1/2023 | 3 | Cumberland | 26 | Chetek-Weyerhaeuser | 16 | |
| 9/8/2023 | 4 | Spooner | 14 | Cumberland | 28 | |
| 9/15/2023 | 5 | Barron | 14 | Cumberland | 28 | |
| 9/22/2023 | 6 | Cumberland | 21 | Bloomer | 8 | |
| 9/29/2023 | 7 | Northwestern | 54 | Cumberland | 0 | |
| 10/6/2023 | 8 | Cumberland | 14 | St. Croix Falls | 48 | |
| 10/13/2023 | 9 | Cameron | 53 | Cumberland | 13 | |