| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Milwaukee King | 66 | Shorewood/Messmer (NC) | 0 | |
| 8/29/2019 | 2 | Kenosha Tremper (NC) | 6 | Milwaukee King | 28 | |
| 9/5/2019 | 3 | Milwaukee Bradley/Milw Arts | 0 | Milwaukee King | 50 | |
| 9/12/2019 | 4 | Milwaukee Washington/Collegiate/Science | 8 | Milwaukee King | 50 | |
| 9/20/2019 | 5 | Milwaukee King | 46 | Milwaukee Hamilton/Audubon | 0 | |
| 9/27/2019 | 6 | Milwaukee King | 20 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 16 | |
| 10/3/2019 | 7 | Milwaukee Riverside/Golda Meir | 21 | Milwaukee King | 28 | |
| 10/10/2019 | 8 | Milwaukee King | 50 | Milwaukee Bay View/Lifelong Learning | 6 | |
| 10/18/2019 | 9 | Milwaukee King | 42 | Milwaukee Reagan (NC) | 20 | |