Round of 32 | Round of 16 | Quarter-Final | Semi-Final | Final | Winner |
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| | | | Lubow - Ucko (1) | | | Fri | SHC 10:30C14 | | | | Cheslock - Goldsmith | | 6-3, 7-5 | | |
| | | | | | | | Lubow - Ucko (1) | | 6-2, 6-1 | | | | | Fri | SHC 12:30QR1 | | | | | | | | Kadow - Morneau | | 6-3, 7-5 | | | | | | |
| | | | | | | | | | | | | | | | Lubow - Ucko (1) | | 6-2, 6-0 | | | | | | | | | | | | | Fri | SHC 2:30 | | | | | | | | | | | | | | | | Shehadi - Urban (4) | | 6-4, 6-0 | | | | | | | | | | | | | | |
| | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | Shehadi - Urban (4) | | 6-3, 6-2 | | | | | | | | | | | | | | | | | | | | | | | | | | | | | Fri | SHC 4:00 | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | Ambrose - Ratner (3) | | 7-5, 6-4 | | | | | | | | | | | | | | | | | | | | | | | | | | | | | | |
| Shehadi - Urban (4) | 3-6, 6-2, 6-2 |
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3 | Kantardjian - Seidenberg | Fri | SHC 9:00C1 | 4 | Cheslock - Goldsmith | | |
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5 | Aversa - Borinsky | | | 6 | Bye | | |
| | | | Aversa - Borinsky | | | Fri | SHC 10:30C16 | | | | Kadow - Morneau | | | | |
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| | | | Aurora - Bibbee | | | Fri | CBCC 10:30C10 | | | | Ellis - Nerenberg | | | | |
| | | | | | | | Ellis - Nerenberg | | 4-6, 6-4, 6-2 | | | | | Fri | SHC 12:30QR2 | | | | | | | | Shehadi - Urban (4) | | 6-4, 6-3 | | | | | | |
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11 | Bye | | | 12 | Ellis - Nerenberg | | |
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13 | Burroughs - Mann | Fri | CBCC 9:00C7 | 14 | Tomic - Vaska | | |
| | | | Burroughs - Mann | | 6-4, 6-1 | Fri | CBCC 10:30C12 | | | | Shehadi - Urban (4) | | | | |
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15 | Bye | | | 16 | Shehadi - Urban (4) | | |
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17 | Ambrose - Ratner (3) | | | 18 | Bye | | |
| | | | Ambrose - Ratner (3) | | | Fri | SHC 10:30C6 | | | | Cummins - Sroczynski | | 6-4, 5-7, 1-0(10-8) | | |
| | | | | | | | Ambrose - Ratner (3) | | 6-2, 6-2 | | | | | Fri | SHC 12:30QR3 | | | | | | | | Maddox - Murray | | 6-2, 6-0 | | | | | | |
| | | | | | | | | | | | | | | | Ambrose - Ratner (3) | | 6-2, 6-3 | | | | | | | | | | | | | Fri | SHC 2:30 | | | | | | | | | | | | | | | | Fawcett - Stulac (2) | | 7-5, 6-2 | | | | | | | | | | | | | | |
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19 | Cummins - Sroczynski | Fri | SHC 9:00C9 | 20 | Collins - Meakem | | |
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21 | Maddox - Murray | | | 22 | Bye | | |
| | | | Maddox - Murray | | | Fri | SHC 10:30C8 | | | | Buckley - Ucko | | | | |
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25 | Atkinson - Combias | | | 26 | Bye | | |
| | | | Atkinson - Combias | | | Fri | CBCC 10:30C2 | | | | Callahan - Dickinson | | | | |
| | | | | | | | Atkinson - Combias | | 6-7, 6-0, 6-2 | | | | | Fri | SHC 12:30QR4 | | | | | | | | Fawcett - Stulac (2) | | 6-4, 6-3 | | | | | | |
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27 | Bye | | | 28 | Callahan - Dickinson | | |
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29 | Byram - Khadduri | Fri | CBCC 9:00C15 | 30 | Cederberg - Ericson | | |
| | | | Byram - Khadduri | | 6-1, 7-6(9-7) | Fri | CBCC 10:30C4 | | | | Fawcett - Stulac (2) | | | | |
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31 | Bye | | | 32 | Fawcett - Stulac (2) | | |
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