Southwest Wisconsin Activities
| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Platteville (NC) | 12 | Cuba City | 7 | |
| 8/30/2019 | 2 | Cuba City | 7 | Black Hawk/Warren IL (NC) | 42 | |
| 9/6/2019 | 3 | Iowa-Grant | 22 | Cuba City | 27 | |
| 9/13/2019 | 4 | Cuba City | 14 | Aquinas | 35 | |
| 9/20/2019 | 5 | Mineral Point | 49 | Cuba City | 6 | |
| 9/27/2019 | 6 | Cuba City | 20 | Lancaster | 49 | |
| 10/4/2019 | 7 | Luther | 21 | Cuba City | 28 | 1OT |
| 10/11/2019 | 8 | Cuba City | 14 | Fennimore | 21 | |
| 10/18/2019 | 9 | Darlington | 40 | Cuba City | 28 | |