| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Brookfield Central (NC) | 43 | South Milwaukee | 6 | |
| 8/25/2023 | 2 | New Berlin Eisenhower (NC) | 14 | South Milwaukee | 32 | |
| 8/31/2023 | 3 | Shorewood/Messmer | 7 | South Milwaukee | 42 | |
| 9/8/2023 | 4 | South Milwaukee | 44 | Cudahy | 8 | |
| 9/15/2023 | 5 | Greendale | 40 | South Milwaukee | 31 | |
| 9/22/2023 | 6 | South Milwaukee | 29 | Greenfield | 60 | |
| 9/29/2023 | 7 | Whitnall | 34 | South Milwaukee | 21 | |
| 10/6/2023 | 8 | South Milwaukee | 0 | Grafton | 53 | |
| 10/13/2023 | 9 | Wisconsin Lutheran | 49 | South Milwaukee | 14 | |