| Round of 16 | Quarter-Final | Semi-Final | Final | Winner |
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| 1 | Rosner - Walden (1) | | | | | 2 | Bye | | | |
| | | | | Rosner - Walden (1) | | Sat | | Sat | CHCC 9:30QR1 | | | | | Cronin - Michalek (former) | | 4-6, 6-3, 7-5 | | | |
| | | | | | | | | Rosner - Walden (1) | | Sat6-1, 6-3 | | | | | | Sat | SHCC 12:00 | | | | | | | | | Resnikoff - Thompson | | 3-6, 7-6, 7-6 | | | | | | | |
| | | | | | | | | | | | | | | | | Rosner - Walden (1) | | Sat6-2, 6-4 | | | | | | | | | | | | | | Sat | SHCC 2:00 | | | | | | | | | | | | | | | | | McConnell - Wilen | | 6-2, 6-3 | | | | | | | | | | | | | | | |
| | McConnell - Wilen | | 6-4, 1-6, 7-6 |
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| 3 | Cronin - Michalek (former) | | Sat | CHCC 8:00C2 | | 4 | Coyne - Young | | | |
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| 5 | Resnikoff - Thompson | | Sat | CHCC 8:00C3 | | 6 | Kindig - Rufus | | | |
| | | | | Resnikoff - Thompson | | Sat6-2, 5-7, 7-5 | | Sat | CHCC 9:30QR2 | | | | | Cohen - Cole | | 6-1, 7-6 | | | |
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| 7 | O'Connor - O'Sullivan | | Sat | CHCC 8:00C4 | | 8 | Cohen - Cole | | | |
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| 9 | Grambling - Staniar | | Sat | SHCC 8:00C5 | | 10 | Carlson - Maddox | | | |
| | | | | Carlson - Maddox | | Sat3-6, 6-3, 7-5 | | Sat | SHCC 9:30QR3 | | | | | DAddario - Stanton | | 7-5, 1-6, 6-4 | | | |
| | | | | | | | | DAddario - Stanton | | Sat2-6, 7-6, 6-0 | | | | | | Sat | SHCC 12:00 | | | | | | | | | McConnell - Wilen | | 6-2, 7-5 | | | | | | | |
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| 11 | Celentano - Pallotta | | Sat | SHCC 8:00C6 | | 12 | DAddario - Stanton | | | |
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| 13 | Olsen - Pallotta | | Sat | SHCC 8:00C7 | | 14 | McConnell - Wilen | | | |
| | | | | McConnell - Wilen | | Sat6-3,7-5 | | Sat | SHCC 9:30QR4 | | | | | Pell - Sweeney (2) | | 7-6, 6-1 | | | |
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| 15 | Combias - Edgar | | Sat | SHCC 8:00C8 | | 16 | Pell - Sweeney (2) | | | |
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