| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Brookwood | 47 | Boscobel (NC) | 6 | |
| 8/30/2019 | 2 | Southwestern/East Dubuque, IL (NC) | 12 | Brookwood | 47 | |
| 9/6/2019 | 3 | Brookwood | 20 | Cashton | 21 | |
| 9/13/2019 | 4 | Brookwood | 35 | Hillsboro | 0 | |
| 9/20/2019 | 5 | Necedah | 0 | Brookwood | 48 | |
| 9/27/2019 | 6 | New Lisbon | 6 | Brookwood | 42 | |
| 10/4/2019 | 7 | Brookwood | 25 | Royall | 0 | |
| 10/11/2019 | 8 | Bangor | 50 | Brookwood | 0 | |
| 10/18/2019 | 9 | Brookwood | 21 | Highland (NC) | 13 | |