| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | New Lisbon (NC) | 22 | Southwestern/East Dubuque, IL | 47 | |
| 8/30/2019 | 2 | Southwestern/East Dubuque, IL | 12 | Brookwood (NC) | 47 | |
| 9/6/2019 | 3 | Cambridge (NC) | 20 | Southwestern/East Dubuque, IL | 12 | |
| 9/13/2019 | 4 | Southwestern/East Dubuque, IL | 53 | Boscobel | 0 | |
| 9/21/2019 | 5 | Pecatonica/Argyle | 11 | Southwestern/East Dubuque, IL | 19 | 1OT |
| 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 | Southwestern/East Dubuque, IL | 0 | Black Hawk/Warren IL | 51 | |
| 10/11/2019 | 8 | Southwestern/East Dubuque, IL | 8 | Potosi/Cassville | 44 | |
| 10/18/2019 | 9 | River Ridge | 47 | Southwestern/East Dubuque, IL | 12 | |