| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Boscobel | 12 | Royall (NC) | 36 | |
| 8/25/2023 | 2 | Boscobel | 13 | Southwestern/East Dubuque, IL (NC) | 40 | |
| 8/31/2023 | 3 | Boscobel | 26 | Iowa-Grant | 42 | |
| 9/8/2023 | 4 | Boscobel | 7 | Highland | 28 | |
| 9/15/2023 | 5 | Hillsboro | 28 | Boscobel | 7 | |
| 9/22/2023 | 6 | Boscobel | 6 | Ithaca | 44 | |
| 9/29/2023 | 7 | Riverdale | 34 | Boscobel | 6 | |
| 10/6/2023 | 8 | New Lisbon | 34 | Boscobel | 26 | |
| 10/13/2023 | 9 | Wauzeka-Steuben/Seneca | 42 | Boscobel | 0 | |