Milwaukee South
Milwaukee City (Blackbourn)
| Date | Week | Home | Score | Away | Score | |
| 8/22/2019 | 1 | Milwaukee South | 12 | Milwaukee Bay View/Lifelong Learning (NC) | 42 | |
| 8/30/2019 | 2 | Milwaukee Madison | 8 | Milwaukee South | 60 | |
| 9/6/2019 | 3 | Milwaukee South | 13 | Milwaukee North | 0 | |
| 9/12/2019 | 4 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 18 | Milwaukee South | 21 | |
| 9/20/2019 | 5 | Milwaukee South | 15 | Obama SCTE | 14 | |
| 9/27/2019 | 6 | Milwaukee South | 8 | Milwaukee Bradley/Milw Arts (NC) | 50 | |
| 10/4/2019 | 7 | Milwaukee Vincent/Destiny | 0 | Milwaukee South | 1 | |
| 10/11/2019 | 8 | Milwaukee South | 0 | Milwaukee Reagan | 44 | |
| 10/17/2019 | 9 | Milwaukee Riverside/Golda Meir (NC) | 35 | Milwaukee South | 7 | |