| | | | 0-0 (0-0) | Non League | Harvard, IL | - | - |
| | | | 0-0 (0-0) | Non League | Racine, WI | - | Watch |
| | | | 0-0 (0-0) | Non League | Walworth, WI | - | - |
| | | | 0-0 (0-0) | Non League | Clinton, WI | - | - |
| | | | 0-0 (0-0) | Non League | Edgerton, WI | - | - |
| | | L 1-3 | 0-1 (0-1) | League | Walworth, WI | - | - |
| | | W 3-0 | 1-1 (1-1) | League | Evansville, WI | - | - |
| | | | 1-1 (1-1) | Non League | Walworth, WI | - | - |
| | | | 1-1 (1-1) | Non League | Kenosha, WI | - | - |
| | | | 1-1 (1-1) | Non League | Walworth, WI | - | - |
| | | L 1-2 | 1-2 (1-1) | Non League | Jefferson, WI | - | - |
| | | W 3-1 | 2-2 (2-1) | League | Beloit, WI | - | - |
| | | W 3-1 | 3-2 (3-1) | League | Walworth, WI | - | - |
| | | L 0-3 | 3-3 (3-2) | League | Walworth, WI | - | - |
| | | L 0-3 | 3-4 (3-3) | League | Brodhead, WI | - | - |
| | | L 0-2 | 3-5 (3-4) | League | Walworth, WI | - | - |
| | | W 2-0 | 4-5 (3-4) | Non League | Walworth, WI | - | - |
| | | W 2-1 | 8-5 (3-4) | Non League | Walworth, WI | - | - |
| | | W 2-1 | 8-5 (3-4) | Non League | Walworth, WI | - | - |
| | | W 2-0 | 8-5 (3-4) | Non League | Walworth, WI | - | - |
| | | W 2-0 | 8-5 (3-4) | Non League | Walworth, WI | - | - |
| | | W 3-0 | 9-5 (4-4) | League | Walworth, WI | - | - |
| | | L 0-3 | 9-6 (4-4) | Non League | Whitefish Bay, WI | - | Watch |