| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Waterloo | 16 | Poynette (NC) | 24 | |
| 8/30/2019 | 2 | Waterloo | 19 | Prairie du Chien (NC) | 46 | |
| 9/6/2019 | 3 | Horicon/Hustisford (NC) | 50 | Waterloo | 20 | |
| 9/13/2019 | 4 | Black Hawk/Warren IL (NC) | 35 | Waterloo | 0 | |
| 9/20/2019 | 5 | Belleville | 22 | Waterloo | 18 | |
| 9/27/2019 | 6 | Waterloo | 42 | Palmyra-Eagle (NC) | 41 | |
| 10/4/2019 | 7 | Marshall | 20 | Waterloo | 9 | |
| 10/11/2019 | 8 | Waterloo | 15 | New Glarus/Monticello | 40 | |
| 10/18/2019 | 9 | Waterloo | 6 | Cambridge | 33 | |