| | | | 0-0 (0-0) | Non League | Lake Forest, IL | - | - |
| | | | 0-0 (0-0) | Non League | Vernon Hills, IL | - | Watch |
| | | W 2-0 | 1-0 (0-0) | Non League | Highland Park, IL | - | Watch |
| | | W 2-0 | 2-0 (0-0) | Non League | Highland Park, IL | - | - |
| | | | 2-0 (0-0) | Non League | Highland Park, IL | - | - |
| | | | 2-0 (0-0) | Non League | Highland Park, IL | - | - |
| | | W 2-0 | 3-0 (1-0) | League | Highland Park, IL | - | Watch |
| | | W 2-1 | 4-0 (2-0) | League | Deerfield, IL | - | Watch |
| | | L 0-2 | 4-1 (2-1) | League | Skokie, IL | - | - |
| | | | 4-1 (2-1) | Non League | Mundelein, IL | - | - |
| | | L 0-2 | 4-2 (2-2) | League | Highland Park, IL | - | Watch |
| | | W 2-0 | 5-2 (2-2) | Non League | Highland Park, IL | - | - |
| | | W 2-0 | 6-2 (3-2) | League | Park Ridge, IL | - | Watch |
| | | W 2-0 | 7-2 (4-2) | League | Des Plaines, IL | - | - |
| | | L 0-2 | 7-3 (4-2) | Non League | Grayslake, IL | - | - |
| | | L 0-2 | 7-4 (4-3) | League | Highland Park, IL | - | - |
| | | L 1-2 | 7-5 (4-4) | League | Highland Park, IL | - | Watch |
| | | L 0-2 | 7-6 (4-5) | League | Highland Park, IL | - | Watch |
| | | W 2-0 | 8-6 (4-5) | Non League | Chicago, IL | - | - |
| | | L 0-2 | 8-7 (4-5) | Non League | Lake Forest, IL | - | Watch |