| | | | 0-0 (0-0) | Non League | Waterloo, WI | - | - |
| | | | 0-0 (0-0) | Non League | Belleville, WI | - | - |
| | | | 0-0 (0-0) | Non League | Marshall, WI | - | - |
| | | L 0-3 | 0-1 (0-0) | Non League | New Glarus, WI | - | - |
| | | L 0-3 | 0-2 (0-0) | Non League | Cambridge, WI | - | - |
| | | L 0-2 | 0-3 (0-0) | Non League | Wonewoc, WI | - | - |
| | | L 0-2 | 2-5 (0-0) | Non League | Wonewoc, WI | - | - |
| | | L 0-2 | 2-5 (0-0) | Non League | Mazomanie, WI | - | - |
| | | W 2-0 | 2-5 (0-0) | Non League | Mazomanie, WI | - | - |
| | | W 2-0 | 2-5 (0-0) | Non League | Mazomanie, WI | - | - |
| | | L 0-3 | 2-6 (0-1) | League | Waterloo, WI | - | - |
| | | W 2-0 | 3-6 (0-1) | Non League | Mazomanie, WI | - | - |
| | | W 2-1 | 4-6 (0-1) | Non League | Darlington, WI | - | - |
| | | W 2-0 | 6-6 (0-1) | Non League | Shullsburg, WI | - | - |
| | | W 2-1 | 6-6 (0-1) | Non League | Blanchardville, WI | - | - |
| | | W 3-1 | 7-6 (1-1) | League | Belleville, WI | - | - |
| | | W 2-0 | 8-6 (1-1) | Non League | Mazomanie, WI | - | - |
| | | W 2-0 | 9-6 (1-1) | Non League | Rio, WI | - | - |
| | | W 2-1 | 10-6 (1-1) | Non League | Mazomanie, WI | - | - |
| | | L 0-3 | 10-7 (1-2) | League | Marshall, WI | - | - |
| | | W 3-0 | 11-7 (2-2) | League | Mazomanie, WI | - | - |
| | | L 0-3 | 11-8 (2-3) | League | Mazomanie, WI | - | - |
| | | W 2-0 | 12-8 (2-3) | Non League | West Salem, WI | - | - |
| | | L 0-2 | 12-9 (2-4) | League | Mazomanie, WI | - | - |
| | | L 1-2 | 12-10 (2-4) | Non League | Mazomanie, WI | - | - |
| | | W 2-0 | 13-10 (2-4) | Non League | Mazomanie, WI | - | - |
| | | W 3-0 | 14-10 (2-4) | Non League | Mazomanie, WI | - | - |
| | | L 0-3 | 14-11 (2-4) | Non League | Mineral Point, WI | - | - |