| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Winnebago Lutheran | 48 | Kettle Moraine Lutheran (NC) | 6 | |
| 8/30/2019 | 2 | Chilton (NC) | 31 | Winnebago Lutheran | 14 | |
| 9/6/2019 | 3 | Winnebago Lutheran | 35 | Laconia | 7 | |
| 9/13/2019 | 4 | Omro | 18 | Winnebago Lutheran | 26 | |
| 9/20/2019 | 5 | Winnebago Lutheran | 46 | North Fond du Lac | 0 | |
| 9/27/2019 | 6 | Winnebago Lutheran | 15 | Saint Mary's Springs | 50 | |
| 10/5/2019 | 7 | Winnebago Lutheran | 10 | Lomira | 12 | |
| 10/11/2019 | 8 | Mayville | 0 | Winnebago Lutheran | 35 | |
| 10/18/2019 | 9 | Marshall (NC) | 0 | Winnebago Lutheran | 56 | |