| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Waupun (NC) | 6 | St. John's NW Academies | 42 | |
| 8/30/2019 | 2 | St. John's NW Academies | 0 | Deerfield (NC) | 1 | |
| 9/6/2019 | 3 | St. John's NW Academies | 0 | Brookfield Academy | 1 | |
| 9/14/2019 | 4 | Living Word Lutheran | 8 | St. John's NW Academies | 41 | |
| 9/20/2019 | 5 | St. John's NW Academies | 28 | Saint Francis | 20 | |
| 9/27/2019 | 6 | Lake Country Lutheran | 41 | St. John's NW Academies | 0 | |
| 10/5/2019 | 7 | St. John's NW Academies | 54 | Hope Christian | 24 | |
| 10/11/2019 | 8 | Kenosha Christian Life (NC) | 7 | St. John's NW Academies | 37 | |
| 10/18/2019 | 9 | St. John's NW Academies | 20 | University School of Milwaukee | 7 | |