| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Ashland | 6 | Northwestern (NC) | 36 | |
| 8/25/2023 | 2 | Ashland | 14 | Hurley (NC) | 28 | |
| 9/1/2023 | 3 | Ashland | 7 | Rhinelander | 32 | |
| 9/8/2023 | 4 | Mosinee | 42 | Ashland | 0 | |
| 9/15/2023 | 5 | Ashland | 6 | Medford | 59 | |
| 9/22/2023 | 6 | Merrill | 6 | Ashland | 7 | |
| 9/28/2023 | 7 | Ashland | 14 | Lakeland | 28 | |
| 10/6/2023 | 8 | Ashland | 0 | Antigo | 15 | |
| 10/13/2023 | 9 | Hayward/Lac Courte Oreilles | 26 | Ashland | 6 | |