| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | New Glarus/Monticello (NC) | 42 | Dodgeville | 7 | |
| 8/30/2019 | 2 | Dodgeville | 27 | Mineral Point (NC) | 62 | |
| 9/6/2019 | 3 | Dodgeville | 6 | Viroqua | 20 | |
| 9/13/2019 | 4 | Richland Center | 10 | Dodgeville | 13 | 1OT |
| 9/20/2019 | 5 | Dodgeville | 14 | Westby | 47 | |
| 9/27/2019 | 6 | Arcadia | 50 | Dodgeville | 8 | |
| 10/4/2019 | 7 | Dodgeville | 6 | Platteville | 55 | |
| 10/11/2019 | 8 | Prairie du Chien | 58 | Dodgeville | 8 | |
| 10/18/2019 | 9 | River Valley | 49 | Dodgeville | 6 | |