| Round 1 |
Cross Town Classic (2) Team 1910 (1) |
| Cross | Caticchio - Kirincic |  | | 1 | | | 6-0, 6-0 | | 1910 | Gottlieb - Kong | |
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| Cross | Cory - Fraley | | | 2 | | | 6-1, 7-6 | | 1910 | Carpenter - Scalabrino | |
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| Cross | Kirincic - Marcelo | | | 3 | | | 6-0, 6-3 | | 1910 | Matheney - Nash | |
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Doggy Paddle Sports (1) G Men (2) |
| Doggy | Horan - Komornik | | | 1 | | | 6-3, 7-5 | | GMen | Gregor - McIlroy | |
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| Doggy | Rosenthal - Weinstein | | | 2 | | | 6-2, 0-6, 1-0 (10-5) | | GMen | Pelser - Windle | |
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| Doggy | Love - Meagher | | | 3 | | | 6-4, 6-1 | | GMen | Becker - Mirchandani | |
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Glenbrook Paddle (0) White Eagle (3) |
| Glenb | Flathers - Levy | | | 1 | | | 6-0, 6-1 | | Eagle | Freeburger - Hayes | |
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| Glenb | Kushnir - Levy | | | 2 | | | 6-2, 6-3 | | Eagle | Burns - Garapati | |
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| Glenb | Comitor - Lieberman | | | 3 | | | 6-3, 6-3 | | Eagle | Cabrera - Rousseau | |
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| Round 2 |
Cross Town Classic (0) G Men (3) |
| Cross | Caticchio - Thurnell | | | 1 | | | 6-1, 6-1 | | GMen | Gregor - McIlroy | |
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| Cross | Cory - Fraley | | | 2 | | | 6-2, 7-6 | | GMen | Pelser - Windle | |
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| Cross | Kirincic - Marcelo | | | 3 | | | 6-0, 6-1 | | GMen | Argie - McIlroy | |
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Doggy Paddle Sports (0) Glenbrook Paddle (3) |
| Doggy | Horan - Komornik | | | 1 | | | 6-0, 6-2 | | Glenb | Flathers - Levy | |
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| Doggy | Rosenthal - Weinstein | | | 2 | | | 6-2, 6-3 | | Glenb | Kushnir - Levy | |
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| Doggy | Love - Meagher | | | 3 | | | 6-3, 6-1 | | Glenb | Comitor - Lieberman | |
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Team 1910 (0) White Eagle (3) |
| 1910 | Kong - Matheney | | | 1 | | | 6-3, 6-2 | | Eagle | Freeburger - Houck | |
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| 1910 | Carpenter - Scalabrino | | | 2 | | | 6-2, 6-2 | | Eagle | Burns - Hayes | |
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| 1910 | Gottlieb - Nash | | | 3 | | | 4-6, 6-3, 1-0 (10-8) | | Eagle | Garapati - Rousseau | |
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| Round 3 |
Cross Town Classic (0) Glenbrook Paddle (3) |
| Cross | Caticchio - Thurnell | | | 1 | | | 4-6, 7-6, 1-0 (10-8) | | Glenb | Flathers - Levy | |
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| Cross | Cory - Fraley | | | 2 | | | 3-6, 6-2, 1-0 (11-9) | | Glenb | Kushnir - Levy | |
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| Cross | Kirincic - Marcelo | | | 3 | | | 6-3, 6-0 | | Glenb | Comitor - Lieberman | |
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Doggy Paddle Sports (0) White Eagle (3) |
| Doggy | Rosenthal - Weinstein | | | 1 | | | 6-4, 7-6 | | Eagle | Burns - Houck | |
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| Doggy | Horan - Komornik | | | 2 | | | 6-1, 6-2 | | Eagle | Cabrera - Freeburger | |
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| Doggy | Love - Meagher | | | 3 | | | 4-6, 6-4, 1-0 (11-9) | | Eagle | Garapati - Johnson | |
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G Men (3) Team 1910 (0) |
| GMen | McIlroy - Pelser | | | 1 | | | 6-0, 6-3 | | 1910 | Kong - Matheney | |
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| GMen | Argie - McIlroy | | | 2 | | | 6-1, 6-0 | | 1910 | Carpenter - Scalabrino | |
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| GMen | Becker - Mirchandani | | | 3 | | | 6-1, 6-1 | | 1910 | Gottlieb - Nash | |
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