| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Hilbert | 42 | Mishicot | 6 | |
| 8/30/2019 | 2 | Hilbert | 56 | Ozaukee | 7 | |
| 9/6/2019 | 3 | Oostburg | 6 | Hilbert | 35 | |
| 9/13/2019 | 4 | Hilbert | 19 | Cedar Grove-Belgium | 0 | |
| 9/20/2019 | 5 | Manitowoc Lutheran | 21 | Hilbert | 60 | |
| 9/27/2019 | 6 | Hilbert | 34 | Random Lake | 7 | |
| 10/4/2019 | 7 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 28 | Hilbert | 62 | |
| 10/11/2019 | 8 | Hilbert | 62 | Howards Grove | 0 | |
| 10/18/2019 | 9 | Reedsville | 8 | Hilbert | 35 | |