| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Milwaukee Vincent/Destiny | 22 | Saint Francis (NC) | 29 | |
| 8/30/2019 | 2 | Obama SCTE | 1 | Milwaukee Vincent/Destiny | 0 | |
| 9/6/2019 | 3 | Milwaukee Vincent/Destiny | 0 | Milwaukee Madison | 1 | |
| 9/13/2019 | 4 | Milwaukee Reagan | 22 | Milwaukee Vincent/Destiny | 14 | |
| 9/20/2019 | 5 | Milwaukee Vincent/Destiny | 0 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 1 | |
| 9/26/2019 | 6 | Milwaukee North | 1 | Milwaukee Vincent/Destiny | 0 | |
| 10/4/2019 | 7 | Milwaukee Vincent/Destiny | 0 | Milwaukee South | 1 | |
| 10/10/2019 | 8 | Milwaukee Vincent/Destiny | 12 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages (NC) | 42 | |