| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Montello/Green Lake/Princeton | 28 | Iola-Scandinavia (NC) | 22 | 1OT |
| 8/30/2019 | 2 | Westfield (NC) | 20 | Montello/Green Lake/Princeton | 44 | |
| 9/6/2019 | 3 | Montello/Green Lake/Princeton | 6 | Markesan | 36 | |
| 9/13/2019 | 4 | Montello/Green Lake/Princeton | 22 | Parkview/Albany | 6 | |
| 9/20/2019 | 5 | Horicon/Hustisford | 44 | Montello/Green Lake/Princeton | 6 | |
| 9/27/2019 | 6 | Montello/Green Lake/Princeton | 6 | Pardeeville | 22 | |
| 10/4/2019 | 7 | Montello/Green Lake/Princeton | 6 | New Glarus/Monticello (NC) | 21 | |
| 10/11/2019 | 8 | Dodgeland | 42 | Montello/Green Lake/Princeton | 24 | |
| 10/18/2019 | 9 | Palmyra-Eagle | 53 | Montello/Green Lake/Princeton | 13 | |