| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Cuba City (NC) | 39 | Benton/Scales Mound IL/Shullsburg | 14 | |
| 8/25/2023 | 2 | Westby (NC) | 68 | Benton/Scales Mound IL/Shullsburg | 22 | |
| 9/1/2023 | 3 | Benton/Scales Mound IL/Shullsburg | 36 | Fennimore | 20 | |
| 9/8/2023 | 4 | Belleville | 59 | Benton/Scales Mound IL/Shullsburg | 14 | |
| 9/15/2023 | 5 | Potosi/Cassville | 52 | Benton/Scales Mound IL/Shullsburg | 6 | |
| 9/22/2023 | 6 | Benton/Scales Mound IL/Shullsburg | 14 | Southwestern/East Dubuque, IL | 48 | |
| 9/29/2023 | 7 | Benton/Scales Mound IL/Shullsburg | 36 | Pecatonica/Argyle | 32 | |
| 10/6/2023 | 8 | Black Hawk/Warren, IL | 60 | Benton/Scales Mound IL/Shullsburg | 0 | |
| 10/13/2023 | 9 | Benton/Scales Mound IL/Shullsburg | 8 | River Ridge | 60 | |