| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Racine Horlick (NC) | 20 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 14 | |
| 8/29/2019 | 2 | Milwaukee Washington/Collegiate/Science | 0 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 42 | |
| 9/6/2019 | 3 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 28 | Milwaukee Hamilton/Audubon | 0 | |
| 9/12/2019 | 4 | Milwaukee Riverside/Golda Meir | 35 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 14 | |
| 9/19/2019 | 5 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 50 | Milwaukee Bay View/Lifelong Learning | 0 | |
| 9/27/2019 | 6 | Milwaukee King | 20 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 16 | |
| 10/4/2019 | 7 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 28 | Milwaukee Bradley/Milw Arts | 6 | |
| 10/10/2019 | 8 | Milwaukee Vincent/Destiny (NC) | 12 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 42 | |
| 10/17/2019 | 9 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 48 | Obama SCTE (NC) | 0 | |