Southwest Wisconsin Activities
| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Platteville (NC) | 7 | Darlington | 34 | |
| 8/25/2023 | 2 | Darlington | 19 | Prairie du Chien (NC) | 21 | |
| 9/1/2023 | 3 | Potosi/Cassville | 8 | Darlington | 41 | |
| 9/8/2023 | 4 | Darlington | 40 | Southwestern/East Dubuque, IL | 0 | |
| 9/15/2023 | 5 | Darlington | 1 | Parkview/Albany | 0 | |
| 9/22/2023 | 6 | Mineral Point | 13 | Darlington | 20 | |
| 9/29/2023 | 7 | Cuba City | 7 | Darlington | 23 | |
| 10/6/2023 | 8 | Belleville | 0 | Darlington | 58 | |
| 10/13/2023 | 9 | Darlington | 49 | Fennimore | 0 | |