| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Kohler/Sheboygan Christian/Sheboygan Lutheran (NC) | 36 | Howards Grove | 20 | |
| 8/25/2023 | 2 | Howards Grove | 55 | Valders (NC) | 6 | |
| 9/1/2023 | 3 | Howards Grove | 13 | Cedar Grove-Belgium | 7 | |
| 9/8/2023 | 4 | Manitowoc Lutheran | 20 | Howards Grove | 28 | |
| 9/15/2023 | 5 | Howards Grove | 42 | Hilbert | 14 | |
| 9/21/2023 | 6 | Oostburg | 35 | Howards Grove | 21 | |
| 9/29/2023 | 7 | Howards Grove | 17 | Reedsville | 26 | |
| 10/6/2023 | 8 | Ozaukee | 7 | Howards Grove | 0 | |
| 10/13/2023 | 9 | Random Lake | 24 | Howards Grove | 0 | |