| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Hillsboro | 6 | Potosi/Cassville (NC) | 50 | |
| 8/30/2019 | 2 | Melrose-Mindoro (NC) | 41 | Hillsboro | 14 | |
| 9/6/2019 | 3 | Bangor | 57 | Hillsboro | 6 | |
| 9/13/2019 | 4 | Brookwood | 35 | Hillsboro | 0 | |
| 9/20/2019 | 5 | Hillsboro | 16 | Cashton | 12 | |
| 9/27/2019 | 6 | Wonewoc-Center/Weston (NC) | 14 | Hillsboro | 42 | |
| 10/4/2019 | 7 | Hillsboro | 30 | Necedah | 12 | |
| 10/11/2019 | 8 | New Lisbon | 0 | Hillsboro | 22 | |
| 10/18/2019 | 9 | Hillsboro | 34 | Royall | 28 | |