| Round of 32 | Round of 16 | Quarter-Final | Semi-Final | Final | Winner |
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| Pi1 | Laird - Straten | | Sat | FCC 8:30PiR1 | | Pi2 | Dunn - Sinha | | | |
| | | | | Dunn - Sinha | | | 6-0, 6-0 | | Sat | FCC 10:15 | | | | | | Elms - Falkner | | 2-6, 7-6, 1-0(11-9) | | | |
| | | | | | | | | Dunn - Sinha | | | 6-1, 6-3, 1-(10-7) | | | | | | | | Sat | FCC 12:00 | | | | | | | | | | | | Daigle - Staub | | 6-1, 6-0 | | | | | | | | | |
| | | | | | | | | | | | | | | | | Daigle - Staub | | | 6-2, 6-1 | | | | | | | | | | | | | | | | | | | | Sun | SHC 9:00 | | | | | | | | | | | | | | | | | | | | | | | | Luey - Rappoport | | 7-6, 6-4 | | | | | | | | | | | | | | | | | | | | | |
| | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | Daigle - Staub | | | 6-1, 7-5 | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | Sun | SHC 10:30 | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | McClintock - Rondepierre | | Default | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | |
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| Pi3 | LoPiccolo - Tooley | | Sat | FCC 8:30PiR2 | | Pi4 | Elms - Falkner | | | |
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| Pi5 | O'Connor - Wisniewski | | Sat | FCC 8:30PiR3 | | Pi6 | Byrne - Cyganovich | | | |
| | | | | O'Connor - Wisniewski | | | 6-4, 2-6, 1-(10-6) | | Sat | FCC 10:15 | | | | | | Daigle - Staub | | 6-4, 6-4 | | | |
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| Pi7 | Daigle - Staub | | Sat | FCC 8:30PiR4 | | Pi8 | Jensen - Mullee | | | |
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| Pi9 | Halper - Porr | | Sat | FCC 9:15PiR5 | | Pi10 | Luey - Rappoport | | | |
| | | | | Luey - Rappoport | | | 6-3, 6-1 | | Sat | FCC 11:00 | | | | | | Durso - Perri | | 7-5, 6-1 | | | |
| | | | | | | | | Luey - Rappoport | | | 6-3, 6-0 | | | | | | | | Sat | FCC 12:00 | | | | | | | | | | | | Schwartz - Weisstuch | | 6-1, 4-6, 1-0(10-8) | | | | | | | | | |
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| Pi11 | Durso - Perri | | Sat | FCC 9:15PiR6 | | Pi12 | Foley - Quirolo | | | |
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| Pi13 | Cussen - Harris | | Sat | FCC 9:15PiR7 | | Pi14 | Brash - Talerman | | | |
| | | | | Brash - Talerman | | | 2-6, 6-2, 1-(10-8) | | Sat | FCC 11:00 | | | | | | Schwartz - Weisstuch | | 6-2, 6-1 | | | |
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| Pi15 | Schwartz - Weisstuch | | Sat | FCC 9:15PiR8 | | Pi16 | Advento - Hamowy | | | |
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| Pi17 | Gardner - Wolff | | Sat | NOE 8:30PiR9 | | Pi18 | Cavanaugh - Keane | | | |
| | | | | Cavanaugh - Keane | | | 6-1, 6-4 | | Sat | NOE 10:15 | | | | | | Churchill - Timoney | | 6-3, 6-2 | | | |
| | | | | | | | | Churchill - Timoney | | | 6-2, 6-4 | | | | | | | | Sat | NOE 12:00 | | | | | | | | | | | | Frankovic - Leonard | | 6-2, 6-1 | | | | | | | | | |
| | | | | | | | | | | | | | | | | Frankovic - Leonard | | | 6-2, 6-1 | | | | | | | | | | | | | | | | | | | | Sun | SHC 9:00 | | | | | | | | | | | | | | | | | | | | | | | | McClintock - Rondepierre | | 6-3, 6-3 | | | | | | | | | | | | | | | | | | | | | |
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| Pi19 | Churchill - Timoney | | Sat | NOE 8:30PiR10 | | Pi20 | Connolly - Reduce | | | |
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| Pi21 | Goodheart - Slattery | | Sat | NOE 8:30PiR11 | | Pi22 | Carr - Freeman | | | |
| | | | | Goodheart - Slattery | | | 3-6, 6-4, 10-7 | | Sat | NOE 10:15 | | | | | | Frankovic - Leonard | | 6-4, 6-0 | | | |
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| Pi23 | Frankovic - Leonard | | Sat | NOE 8:30PiR12 | | Pi24 | Maiorano - Mayer | | | |
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| Pi25 | Boiardi - DiClemente | | Sat | NOE 9:15PiR13 | | Pi26 | Dyer - Matzinger | | | |
| | | | | Boiardi - DiClemente | | | 6-1, 6-0 | | Sat | NOE 11:00 | | | | | | Friedman - Wissel | | 6-3, 6-3 | | | |
| | | | | | | | | Boiardi - DiClemente | | | 6-3, 6-1 | | | | | | | | Sat | NOE 12:00 | | | | | | | | | | | | McClintock - Rondepierre | | 5-7, 7-5, 10-6 | | | | | | | | | |
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| Pi27 | Friedman - Wissel | | Sat | NOE 9:15PiR14 | | Pi28 | DePaul - Shah | | | |
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| Pi29 | Krishnan - Weck | | Sat | NOE 9:15PiR15 | | Pi30 | Grainger - Singh | | | |
| | | | | Grainger - Singh | | | 6-4, 6-3 | | Sat | NOE 11:00 | | | | | | McClintock - Rondepierre | | 6-3, 3-6, 11-9 | | | |
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| Pi31 | McClintock - Rondepierre | | Sat | NOE 9:15PiR16 | | Pi32 | Bayvel - Scura | | | |
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