| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Medford | 24 | New Richmond (NC) | 44 | |
| 8/25/2023 | 2 | Onalaska (NC) | 35 | Medford | 52 | |
| 9/1/2023 | 3 | Merrill | 0 | Medford | 12 | |
| 9/8/2023 | 4 | Medford | 50 | Lakeland | 14 | |
| 9/15/2023 | 5 | Ashland | 6 | Medford | 59 | |
| 9/22/2023 | 6 | Medford | 36 | Hayward/Lac Courte Oreilles | 7 | |
| 9/29/2023 | 7 | Rhinelander | 8 | Medford | 40 | |
| 10/6/2023 | 8 | Medford | 0 | Mosinee | 14 | |
| 10/13/2023 | 9 | Antigo | 14 | Medford | 58 | |