| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Highland | 7 | River Ridge (NC) | 14 | |
| 8/25/2023 | 2 | Black Hawk/Warren, IL (NC) | 42 | Highland | 6 | |
| 9/1/2023 | 3 | Wauzeka-Steuben/Seneca | 0 | Highland | 21 | |
| 9/8/2023 | 4 | Boscobel | 7 | Highland | 28 | |
| 9/15/2023 | 5 | Highland | 29 | Ithaca | 0 | |
| 9/22/2023 | 6 | Royall | 34 | Highland | 30 | |
| 9/29/2023 | 7 | Iowa-Grant | 8 | Highland | 31 | |
| 10/7/2023 | 8 | Highland | 29 | Hillsboro | 0 | |
| 10/13/2023 | 9 | Riverdale | 8 | Highland | 47 | |