| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Baraboo (NC) | 15 | Milton | 55 | |
| 8/30/2019 | 2 | Milton | 40 | Mount Horeb/Barneveld (NC) | 0 | |
| 9/6/2019 | 3 | Milton | 41 | Fort Atkinson | 7 | |
| 9/13/2019 | 4 | Monona Grove | 20 | Milton | 27 | |
| 9/20/2019 | 5 | Milton | 47 | Oregon | 26 | |
| 9/27/2019 | 6 | Stoughton | 21 | Milton | 28 | 2OT |
| 10/4/2019 | 7 | Milton | 28 | Monroe | 34 | |
| 10/11/2019 | 8 | Edgewood | 0 | Milton | 40 | |
| 10/18/2019 | 9 | Watertown | 27 | Milton | 41 | |