| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Jefferson | 7 | Watertown Luther Prep (NC) | 35 | |
| 8/25/2023 | 2 | Fort Atkinson (NC) | 34 | Jefferson | 27 | |
| 9/1/2023 | 3 | Jefferson | 35 | Whitewater | 14 | |
| 9/8/2023 | 4 | McFarland | 41 | Jefferson | 21 | |
| 9/15/2023 | 5 | Jefferson | 10 | Monroe | 27 | |
| 9/22/2023 | 6 | Evansville | 23 | Jefferson | 20 | |
| 9/29/2023 | 7 | Delavan-Darien | 6 | Jefferson | 9 | |
| 10/6/2023 | 8 | Jefferson | 28 | Edgerton | 18 | |
| 10/13/2023 | 9 | *Jefferson | 41 | Parkview Christian (IL) (NC) | 6 | |
| 10/13/2023 | 9 | Jefferson | 1 | East Troy | 0 | |