| Date | Week | Home | Score | Away | Score | |
| 8/17/2018 | 1 | Grantsburg (NC) | 35 | Cumberland | 28 | |
| 8/24/2018 | 2 | Cumberland | 56 | Cameron (NC) | 6 | |
| 8/31/2018 | 3 | Cumberland | 20 | Northwestern | 48 | |
| 9/7/2018 | 4 | Cumberland | 46 | Barron | 6 | |
| 9/14/2018 | 5 | Cumberland | 64 | Chetek-Weyerhaeuser | 26 | |
| 9/21/2018 | 6 | Cumberland | 36 | Bloomer | 22 | |
| 9/28/2018 | 7 | Cumberland | 38 | Hayward/La Courte Oreilles | 18 | |
| 10/5/2018 | 8 | Cumberland | 0 | Spooner | 42 | |
| 10/12/2018 | 9 | Ladysmith | 22 | Cumberland | 47 | |