| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Ripon (NC) | 26 | Watertown Luther Prep | 35 | |
| 8/30/2019 | 2 | Kettle Moraine Lutheran (NC) | 19 | Watertown Luther Prep | 42 | |
| 9/6/2019 | 3 | Watertown Luther Prep | 7 | Saint Mary's Springs (NC) | 48 | |
| 9/13/2019 | 4 | Watertown Luther Prep | 10 | Cambridge (NC) | 20 | |
| 9/20/2019 | 5 | Watertown Luther Prep | 6 | Lodi | 27 | |
| 9/27/2019 | 6 | Lakeside Lutheran | 7 | Watertown Luther Prep | 9 | |
| 10/4/2019 | 7 | Poynette | 21 | Watertown Luther Prep | 26 | |
| 10/11/2019 | 8 | Watertown Luther Prep | 7 | Columbus | 14 | |
| 10/18/2019 | 9 | Watertown Luther Prep | 8 | Lake Mills | 54 | |