| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | New Glarus/Monticello | 42 | Dodgeville (NC) | 7 | |
| 8/30/2019 | 2 | Lake Mills (NC) | 55 | New Glarus/Monticello | 21 | |
| 9/6/2019 | 3 | Columbus (NC) | 46 | New Glarus/Monticello | 17 | |
| 9/13/2019 | 4 | New Glarus/Monticello | 7 | Lodi (NC) | 44 | |
| 9/20/2019 | 5 | Marshall | 7 | New Glarus/Monticello | 33 | |
| 9/27/2019 | 6 | New Glarus/Monticello | 7 | Cambridge | 28 | |
| 10/4/2019 | 7 | Montello/Green Lake/Princeton (NC) | 6 | New Glarus/Monticello | 21 | |
| 10/11/2019 | 8 | Waterloo | 15 | New Glarus/Monticello | 40 | |
| 10/18/2019 | 9 | New Glarus/Monticello | 42 | Belleville | 7 | |