| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | University School of Milwaukee | 10 | Catholic Central (NC) | 9 | |
| 8/30/2019 | 2 | Martin Luther (NC) | 35 | University School of Milwaukee | 14 | |
| 9/6/2019 | 3 | University School of Milwaukee | 43 | Saint Francis | 14 | |
| 9/13/2019 | 4 | Kenosha Christian Life (NC) | 0 | University School of Milwaukee | 28 | |
| 9/20/2019 | 5 | University School of Milwaukee | 0 | Lake Country Lutheran | 39 | |
| 9/28/2019 | 6 | Hope Christian | 6 | University School of Milwaukee | 40 | |
| 10/4/2019 | 7 | Brookfield Academy | 21 | University School of Milwaukee | 6 | |
| 10/11/2019 | 8 | University School of Milwaukee | 54 | Living Word Lutheran | 8 | |
| 10/18/2019 | 9 | St. John's NW Academies | 20 | University School of Milwaukee | 7 | |