| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Oostburg | 45 | Howards Grove | 0 | |
| 8/30/2019 | 2 | Howards Grove | 8 | Cedar Grove-Belgium | 42 | |
| 9/6/2019 | 3 | Manitowoc Lutheran | 7 | Howards Grove | 48 | |
| 9/13/2019 | 4 | Howards Grove | 6 | Random Lake | 21 | |
| 9/20/2019 | 5 | Kohler/Sheboygan Lutheran/Sheboygan Christian | 54 | Howards Grove | 53 | |
| 9/27/2019 | 6 | Mishicot | 36 | Howards Grove | 19 | |
| 10/4/2019 | 7 | Howards Grove | 22 | Reedsville | 20 | |
| 10/11/2019 | 8 | Hilbert | 62 | Howards Grove | 0 | |
| 10/18/2019 | 9 | Howards Grove | 20 | Ozaukee | 33 | |