| Date | Week | Home | Score | Away | Score | |
| 8/19/2021 | 1 | Spencer/Columbus Catholic (NC) | 51 | Glenwood City | 28 | |
| 8/27/2021 | 2 | Barron (NC) | 8 | Glenwood City | 15 | |
| 9/3/2021 | 3 | Turtle Lake | 12 | Glenwood City | 24 | |
| 9/10/2021 | 4 | Glenwood City | 20 | Elmwood/Plum City | 32 | |
| 9/17/2021 | 5 | Spring Valley | 42 | Glenwood City | 10 | |
| 9/24/2021 | 6 | Glenwood City | 45 | Clear Lake | 22 | |
| 10/1/2021 | 7 | Cadott | 13 | Glenwood City | 32 | |
| 10/8/2021 | 8 | Boyceville | 24 | Glenwood City | 10 | |
| 10/15/2021 | 9 | Glenwood City | 55 | Colfax | 0 | |