| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Plymouth | 24 | New Berlin Eisenhower (NC) | 27 | |
| 8/30/2019 | 2 | Sheboygan Falls (NC) | 7 | Plymouth | 14 | |
| 9/6/2019 | 3 | Plymouth | 28 | Ripon | 10 | |
| 9/13/2019 | 4 | Plymouth | 35 | Berlin | 7 | |
| 9/20/2019 | 5 | Campbellsport | 0 | Plymouth | 43 | |
| 9/27/2019 | 6 | Plymouth | 66 | Kewaskum | 0 | |
| 10/4/2019 | 7 | Kettle Moraine Lutheran | 0 | Plymouth | 44 | |
| 10/11/2019 | 8 | Plymouth | 42 | Winneconne | 0 | |
| 10/18/2019 | 9 | Waupun | 6 | Plymouth | 62 | |