Southwest Wisconsin Activities
| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Darlington | 20 | Westby (NC) | 12 | |
| 8/30/2019 | 2 | Lake Country Lutheran (NC) | 26 | Darlington | 27 | 1OT |
| 9/6/2019 | 3 | Darlington | 21 | Lancaster | 46 | |
| 9/13/2019 | 4 | Iowa-Grant | 0 | Darlington | 36 | |
| 9/20/2019 | 5 | Darlington | 34 | Luther | 9 | |
| 9/27/2019 | 6 | Aquinas | 14 | Darlington | 0 | |
| 10/4/2019 | 7 | Darlington | 22 | Fennimore | 8 | |
| 10/11/2019 | 8 | Mineral Point | 47 | Darlington | 16 | |
| 10/18/2019 | 9 | Darlington | 40 | Cuba City | 28 | |