| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Waterford | 15 | Kenosha Bradford/Reuther (NC) | 0 | |
| 8/29/2019 | 2 | Waterford | 35 | Oak Creek (NC) | 7 | |
| 9/6/2019 | 3 | Union Grove | 22 | Waterford | 42 | |
| 9/13/2019 | 4 | Waterford | 47 | Wilmot | 14 | |
| 9/20/2019 | 5 | Waterford | 56 | Westosha Central | 7 | |
| 9/27/2019 | 6 | Elkhorn | 0 | Waterford | 42 | |
| 10/4/2019 | 7 | Waterford | 41 | Delavan-Darien | 6 | |
| 10/11/2019 | 8 | Burlington | 14 | Waterford | 49 | |
| 10/18/2019 | 9 | Badger | 17 | Waterford | 7 | |