| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Royall (NC) | 0 | Benton/Scales Mound IL/Shullsburg | 35 | |
| 8/30/2019 | 2 | Benton/Scales Mound IL/Shullsburg | 28 | Cambridge (NC) | 0 | |
| 9/6/2019 | 3 | Benton/Scales Mound IL/Shullsburg | | Pecatonica/Argyle | | |
| 9/6/2019 | 3 | Benton/Scales Mound IL/Shullsburg | 32 | Pecatonica/Argyle | 8 | |
| 9/13/2019 | 4 | Potosi/Cassville | 12 | Benton/Scales Mound IL/Shullsburg | 20 | |
| 9/20/2019 | 5 | Black Hawk/Warren IL | 33 | Benton/Scales Mound IL/Shullsburg | 6 | |
| 9/27/2019 | 6 | Benton/Scales Mound IL/Shullsburg | | Southwestern/East Dubuque, IL | | |
| 9/27/2019 | 6 | Benton/Scales Mound IL/Shullsburg | 50 | Southwestern/East Dubuque, IL | 13 | |
| 10/4/2019 | 7 | Boscobel | 6 | Benton/Scales Mound IL/Shullsburg | 38 | |
| 10/11/2019 | 8 | Benton/Scales Mound IL/Shullsburg | | River Ridge | | |
| 10/11/2019 | 8 | Benton/Scales Mound IL/Shullsburg | 30 | River Ridge | 14 | |