| Date | Week | Home | Score | Away | Score | |
| 8/20/2021 | 1 | Rice Lake (NC) | 28 | Medford | 6 | |
| 8/27/2021 | 2 | Medford | 14 | Amherst (NC) | 29 | |
| 9/3/2021 | 3 | Medford | 30 | Ashland | 14 | |
| 9/10/2021 | 4 | Lakeland | 20 | Medford | 45 | |
| 9/17/2021 | 5 | Medford | 14 | Rhinelander | 28 | |
| 9/24/2021 | 6 | Hayward/Lac Courte Oreilles | 20 | Medford | 30 | |
| 10/1/2021 | 7 | Antigo | 0 | Medford | 40 | |
| 10/8/2021 | 8 | Medford | 14 | Mosinee | 41 | |
| 10/15/2021 | 9 | Merrill | 12 | Medford | 30 | |