| Round of 16 | Quarter-Final | Semi-Final | Final | Winner |
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| 1 | Dardis - Shay (1) | | | | | 2 | Bye | | | |
| | | | | Dardis - Shay (1) | | | | Fri | HCC 9:30QR1 | | | | | Hughes - Humphrey | | 6-1, 6-2 | | | |
| | | | | | | | | Dardis - Shay (1) | | 6-3, 6-1 | | | | | | Fri | HCC 11:30S1 | | | | | | | | | O'Connor - Rogers (4) | | 4-6, 6-2, 6-2 | | | | | | | |
| | | | | | | | | | | | | | | | | Dardis - Shay (1) | | 0-6, 6-2, 6-1 | | | | | | | | | | | | | | Fri | HCC 2:30 | | | | | | | | | | | | | | | | | Jaffe - Rudloff (3) | | 2-6, 6-4, 6-2 | | | | | | | | | | | | | | | |
| | Jaffe - Rudloff (3) | | 6-7(6-8), 6-3, 6-2 |
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| 3 | Neri - Reynolds | | Fri | HCC 8:30C2 | | 4 | Hughes - Humphrey | | | |
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| 5 | Coughlin - Schneider | | Fri | HCC 8:30C3 | | 6 | Garvey - Mackool | | | |
| | | | | Coughlin - Schneider | | 6-1, 6-0 | | Fri | HCC 9:30QR2 | | | | | O'Connor - Rogers (4) | | 6-0, 6-0 | | | |
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| 7 | Finnegan - Hartmann | | Fri | HCC 8:30C4 | | 8 | O'Connor - Rogers (4) | | | |
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| 9 | Jaffe - Rudloff (3) | | Fri | HBC 8:30C5 | | 10 | Serignese - Taylor | | | |
| | | | | Jaffe - Rudloff (3) | | 6-0, 6-0 | | Fri | HBC 9:30QR3 | | | | | Kriskey - Stuhr | | 6-2, 6-1 | | | |
| | | | | | | | | Jaffe - Rudloff (3) | | 6-4, 6-3 | | | | | | Fri | HCC 11:30S2 | | | | | | | | | Flynn - Mangan (2) | | 6-2, 6-3 | | | | | | | |
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| 11 | Annunziato - Driscoll | | Fri | HBC 8:30C6 | | 12 | Kriskey - Stuhr | | | |
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| 13 | Brown - O'Donnell | | Fri | HCC 8:30C7 | | 14 | Callaghan - Haskell | | | |
| | | | | Brown - O'Donnell | | 6-2, 6-1 | | Fri | HCC 9:30QR4 | | | | | Flynn - Mangan (2) | | | | | |
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| 15 | Bye | | | | | 16 | Flynn - Mangan (2) | | | |
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