| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Cedar Grove-Belgium | 56 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 6 | |
| 8/30/2019 | 2 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 50 | Manitowoc Lutheran | 28 | |
| 9/6/2019 | 3 | Random Lake | 43 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 21 | |
| 9/13/2019 | 4 | Mishicot | 22 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 26 | |
| 9/20/2019 | 5 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 54 | Howards Grove | 53 | |
| 9/27/2019 | 6 | Reedsville | 44 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 38 | |
| 10/4/2019 | 7 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 28 | Hilbert | 62 | |
| 10/11/2019 | 8 | Ozaukee | 44 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 20 | |
| 10/18/2019 | 9 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 34 | Oostburg | 57 | |