Milwaukee City (Blackbourn)
| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Roncalli (NC) | 48 | Obama SCTE | 8 | |
| 8/30/2019 | 2 | Obama SCTE | 1 | Milwaukee Vincent/Destiny | 0 | |
| 9/6/2019 | 3 | Milwaukee Reagan | 38 | Obama SCTE | 0 | |
| 9/13/2019 | 4 | Obama SCTE | 46 | Milwaukee North | 6 | |
| 9/20/2019 | 5 | Milwaukee South | 15 | Obama SCTE | 14 | |
| 9/27/2019 | 6 | Obama SCTE | 0 | Milwaukee Pulaski/Carmen South/Carmen Southeast | 1 | |
| 10/3/2019 | 7 | Milwaukee Washington/Collegiate/Science (NC) | 18 | Obama SCTE | 12 | |
| 10/11/2019 | 8 | Obama SCTE | 62 | Milwaukee Madison | 0 | |
| 10/17/2019 | 9 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages (NC) | 48 | Obama SCTE | 0 | |