| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | New Lisbon | 22 | Southwestern/East Dubuque, IL (NC) | 47 | |
| 8/30/2019 | 2 | Boscobel (NC) | 6 | New Lisbon | 45 | |
| 9/6/2019 | 3 | New Lisbon | 45 | North Crawford (NC) | 0 | |
| 9/13/2019 | 4 | Royall | 16 | New Lisbon | 20 | |
| 9/20/2019 | 5 | Bangor | 55 | New Lisbon | 12 | |
| 9/27/2019 | 6 | New Lisbon | 6 | Brookwood | 42 | |
| 10/4/2019 | 7 | Cashton | 26 | New Lisbon | 14 | |
| 10/11/2019 | 8 | New Lisbon | 0 | Hillsboro | 22 | |
| 10/18/2019 | 9 | New Lisbon | 14 | Necedah | 32 | |