| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Pewaukee (NC) | 9 | Milwaukee Riverside/Golda Meir | 14 | |
| 8/30/2019 | 2 | Milwaukee Bay View/Lifelong Learning | 0 | Milwaukee Riverside/Golda Meir | 57 | |
| 9/6/2019 | 3 | Milwaukee Riverside/Golda Meir | 57 | Milwaukee Washington/Collegiate/Science | 0 | |
| 9/12/2019 | 4 | Milwaukee Riverside/Golda Meir | 35 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 14 | |
| 9/20/2019 | 5 | Milwaukee Reagan (NC) | 8 | Milwaukee Riverside/Golda Meir | 20 | |
| 9/28/2019 | 6 | Milwaukee Hamilton/Audubon | 8 | Milwaukee Riverside/Golda Meir | 43 | |
| 10/3/2019 | 7 | Milwaukee Riverside/Golda Meir | 21 | Milwaukee King | 28 | |
| 10/12/2019 | 8 | Milwaukee Bradley/Milw Arts | 6 | Milwaukee Riverside/Golda Meir | 46 | |
| 10/17/2019 | 9 | Milwaukee Riverside/Golda Meir | 35 | Milwaukee South (NC) | 7 | |