| Date | Week | Home | Score | Away | Score | |
| 8/20/2021 | 1 | Highland | 34 | River Ridge (NC) | 12 | |
| 8/27/2021 | 2 | Independence/Gilmanton (NC) | 0 | Highland | 28 | |
| 9/3/2021 | 3 | Boscobel | 14 | Highland | 47 | |
| 9/10/2021 | 4 | Highland | 29 | Ithaca | 21 | |
| 9/17/2021 | 5 | Cashton | 20 | Highland | 27 | |
| 9/24/2021 | 6 | Riverdale | 6 | Highland | 52 | |
| 10/1/2021 | 7 | Highland | 42 | De Soto | 2 | |
| 10/9/2021 | 8 | Highland | 58 | Hillsboro | 2 | |
| 10/15/2021 | 9 | Wauzeka-Steuben/Seneca | 8 | Highland | 44 | |