| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Cambridge | 29 | Brookfield Academy (NC) | 28 | |
| 8/30/2019 | 2 | Benton/Scales Mound IL/Shullsburg (NC) | 28 | Cambridge | 0 | |
| 9/6/2019 | 3 | Cambridge | 20 | Southwestern/East Dubuque, IL (NC) | 12 | |
| 9/13/2019 | 4 | Watertown Luther Prep (NC) | 10 | Cambridge | 20 | |
| 9/20/2019 | 5 | Boscobel (NC) | 14 | Cambridge | 49 | |
| 9/27/2019 | 6 | New Glarus/Monticello | 7 | Cambridge | 28 | |
| 10/4/2019 | 7 | Cambridge | 14 | Belleville | 7 | |
| 10/11/2019 | 8 | Cambridge | 23 | Marshall | 13 | |
| 10/18/2019 | 9 | Waterloo | 6 | Cambridge | 33 | |