| Round 1 |
| Barrington Broncos (0) | |
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| No Excuses (3) | |
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| Barri | Talbot - Talbot (51.6) | | | 1 | EV | 6-3, 6-2 | | NoExc | Kauffman - Sunseri (60.1) |  |
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| Barri | DeGrazia - Fitch (74.6) | | | 2 | EV | 6-4, 6-3 | | NoExc | Barrett - Churton (65.9) | |
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| Barri | Habib - Smith (86.8) | | | 3 | EV | 2-6, 6-4, 1-0 | | NoExc | Mackey - Metz (81.7) | |
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| Grosse Pointe Blanks (2) | |
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| Radley Run 23 (1) | |
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| Gross | Brink - Rizzo (61.3) | | | 1 | EV | 6-3, 3-6, 1-0 | | Radle | Haines - Wheeler (63.1) | |
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| Gross | Studders - Terry (68.0) | | | 2 | EV | 6-1, 6-4 | | Radle | Strong - Venema (73.0) | |
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| Gross | Backman - Hix (69.7) | | | 3 | EV | 6-3, 6-3 | | Radle | Amsbaugh - Stanislawczyk (75.2) | |
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| How's Your Sigma (1) | |
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| Midtown Chicago (2) | |
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| Hsyrs | Griesser - Morris (55.9) | | | 1 | EV | 6-3, 6-3 | | Midto | Anliker - Toepke (57.5) | |
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| Hsyrs | Butler - McCarthy (68.4) | | | 2 | EV | 6-2, 7-6 | | Midto | Syftestad - Wiltshire (74.7) | |
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| Hsyrs | Herbenick - Schoen (78.2) | | | 3 | EV | 6-2, 6-1 | | Midto | Patterson - Vigerust (76.3) | |
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| Round 2 |
| Barrington Broncos (0) | |
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| Midtown Chicago (3) | |
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| Barri | Habib - Talbot (58.2) | | | 1 | EV | 6-3, 6-4 | | Midto | Anliker - Toepke (57.5) | |
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| Barri | DeGrazia - Talbot (70.9) | | | 2 | EV | 6-4, 6-4 | | Midto | Patterson - Syftestad (68.6) | |
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| Barri | Berry - Smith (105.5) | | | 3 | EV | 6-3, 6-2 | | Midto | Vigerust - Wiltshire (82.3) | |
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| Grosse Pointe Blanks (0) | |
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| No Excuses (3) | |
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| Gross | Brink - Terry (61.9) | | | 1 | EV | 7-5, 6-1 | | NoExc | Kauffman - Sunseri (60.1) | |
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| Gross | Hix - Rizzo (64.9) | | | 2 | EV | 6-2, 6-4 | | NoExc | Barrett - Churton (65.9) | |
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| Gross | Jones - Studders (80.3) | | | 3 | EV | 6-2, 6-3 | | NoExc | Mackey - Metz (81.7) | |
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| How's Your Sigma (2) | |
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| Radley Run 23 (1) | |
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| Hsyrs | Griesser - McCarthy (58.6) | | | 1 | EV | 6-1, 6-1 | | Radle | Haines - Wheeler (63.1) | |
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| Hsyrs | Butler - Morris (65.7) | | | 2 | EV | 6-4, 3-6, 1-0 | | Radle | Strong - Venema (73.0) | |
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| Hsyrs | Herbenick - Schoen (78.2) | | | 3 | EV | 6-4, 6-1 | | Radle | Amsbaugh - Stanislawczyk (75.2) | |
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| Round 3 |
| Barrington Broncos (1) | |
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| Radley Run 23 (2) | |
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| Barri | Smith - Talbot (70.2) | | | 1 | EV | 6-2, 6-4 | | Radle | Haines - Wheeler (63.1) | |
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| Barri | DeGrazia - Talbot (70.9) | | | 2 | EV | 4-6, 6-2, 1-0 | | Radle | Strong - Venema (73.0) | |
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| Barri | Berry - Habib (93.6) | | | 3 | EV | 6-1, 6-1 | | Radle | Amsbaugh - Stanislawczyk (75.2) | |
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| Grosse Pointe Blanks (2) | |
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| How's Your Sigma (1) | |
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| Gross | Brink - Terry (61.9) | | | 1 | EV | 6-2, 6-3 | | Hsyrs | Griesser - McCarthy (58.6) | |
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| Gross | Backman - Hix (69.7) | | | 2 | EV | 7-5, 6-1 | | Hsyrs | Butler - Morris (65.7) | |
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| Gross | Jones - Rizzo (78.1) | | | 3 | EV | 6-2, 7-6 | | Hsyrs | Herbenick - Schoen (78.2) | |
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| Midtown Chicago (1) | |
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| No Excuses (2) | |
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| Midto | Anliker - Toepke (57.5) | | | 1 | EV | 6-3, 6-4 | | NoExc | Kauffman - Sunseri (60.1) | |
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| Midto | Patterson - Syftestad (68.6) | | | 2 | EV | 6-4, 3-6, 1-0 | | NoExc | Barrett - Churton (65.9) | |
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| Midto | Vigerust - Wiltshire (82.3) | | | 3 | EV | 6-2, 3-6, 1-0 | | NoExc | Mackey - Metz (81.7) | |
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