| Date | Week | Home | Score | Away | Score | |
| 8/22/2019 | 1 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 0 | Milwaukee Reagan | 44 | |
| 9/5/2019 | 3 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 8 | Milwaukee Bay View/Lifelong Learning (NC) | 56 | |
| 9/12/2019 | 4 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 18 | Milwaukee South | 21 | |
| 9/20/2019 | 5 | Milwaukee Vincent/Destiny | 0 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 1 | |
| 9/27/2019 | 6 | Obama SCTE | 0 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 1 | |
| 10/4/2019 | 7 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 48 | Milwaukee Madison | 8 | |
| 10/11/2019 | 8 | Milwaukee North | 14 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 36 | |
| 10/17/2019 | 9 | Milwaukee Hamilton/Audubon (NC) | 40 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 14 | |