| Round of 16 | Quarter-Final | Semi-Final | Final | Winner |
|---|
| 1 | McKessy - Wadehra (1) | | | | | 2 | Bye | | | |
| | | | | McKessy - Wadehra (1) | | | | Sat | CHTC 10:30C5 | | | | | Narayan - Pastoor | | 6-0,6-2 | | | |
| | | | | | | | | McKessy - Wadehra (1) | | 6-2,6-1 | | | | | | Sat | CHTC 12:30R1 | | | | | | | | | Barrickman - Megill (former) | | 7-6(7-2),5-7,6-2 | | | | | | | |
| | | | | | | | | | | | | | | | | McKessy - Wadehra (1) | | 7-6(7-2),6-2 | | | | | | | | | | | | | | Sat | CHTC 3:00 | | | | | | | | | | | | | | | | | Beverley - Pritchett | | 6-1,7-6(7-4) | | | | | | | | | | | | | | | |
| | McKessy - Wadehra (1) | | 6-4,7-6 |
|
| 3 | Crick - MacAdam | | Sat | CHTC 8:45C1 | | 4 | Narayan - Pastoor | | | |
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| 5 | Barrickman - Megill (former) | | | | | 6 | Bye | | | |
| | | | | Barrickman - Megill (former) | | | | Sat | CHTC 9:30C3 | | | | | Nebiker - Walsh | | | | | |
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| | | | | Green - Zaluski | | | | Sat | CHTC 9:30C4 | | | | | Collins - Horine | | | | | |
| | | | | | | | | Green - Zaluski | | 6-1,6-2 | | | | | | Sat | CHTC 12:30R2 | | | | | | | | | Beverley - Pritchett | | 6-4,6-3 | | | | | | | |
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| 11 | Collins - Horine | | | | | 12 | Bye | | | |
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| 13 | Barrickman - Megill | | Sat | CHTC 8:45C2 | | 14 | Beverley - Pritchett | | | |
| | | | | Beverley - Pritchett | | 6-4,6-1 | | Sat | CHTC 10:30C7 | | | | | Brown - Donovan (2) | | | | | |
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| 15 | Bye | | | | | 16 | Brown - Donovan (2) | | | |
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