| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Brookwood (NC) | 47 | Boscobel | 6 | |
| 8/30/2019 | 2 | Boscobel | 6 | New Lisbon (NC) | 45 | |
| 9/6/2019 | 3 | River Ridge | 58 | Boscobel | 0 | |
| 9/13/2019 | 4 | Southwestern/East Dubuque, IL | 53 | Boscobel | 0 | |
| 9/20/2019 | 5 | Boscobel | 14 | Cambridge (NC) | 49 | |
| 9/28/2019 | 6 | Pecatonica/Argyle | 51 | Boscobel | 6 | |
| 10/4/2019 | 7 | Boscobel | 6 | Benton/Scales Mound IL/Shullsburg | 38 | |
| 10/12/2019 | 8 | Black Hawk/Warren IL | 55 | Boscobel | 0 | |
| 10/18/2019 | 9 | Boscobel | 0 | Potosi/Cassville | 40 | |