Milwaukee North
Milwaukee City (Blackbourn)
| Date | Week | Home | Score | Away | Score | |
| 8/30/2019 | 2 | Milwaukee North | 0 | Delavan-Darien (NC) | 50 | |
| 9/6/2019 | 3 | Milwaukee South | 13 | Milwaukee North | 0 | |
| 9/13/2019 | 4 | Obama SCTE | 46 | Milwaukee North | 6 | |
| 9/20/2019 | 5 | Milwaukee North | 40 | Milwaukee Madison | 0 | |
| 9/26/2019 | 6 | Milwaukee North | 1 | Milwaukee Vincent/Destiny | 0 | |
| 10/5/2019 | 7 | Milwaukee Reagan | 66 | Milwaukee North | 0 | |
| 10/11/2019 | 8 | Milwaukee North | 14 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 36 | |