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| 09-Jun-09 - 14:00 Los Angeles - | First Round | Blue Star | 2-5 | Sonoma | | |
| 09-Jun-09 - 17:00 Chicago | First Round | Fire PDL | 3-1 | Bavarians | | |
| 09-Jun-09 - 19:00 Los Angeles | First Round | Kitsap | 0-3 | Portland | | |
| 09-Jun-09 - 19:00 New York | First Round | West Mass | 3-2 | Emigrante | | |
| 09-Jun-09 - 19:00 New York | First Round | NC | 2-1 | Richmond | | |
| 09-Jun-09 - 19:00 New York | First Round | Wilmngton | 2-0 | Charlotte | | |
| 09-Jun-09 - 19:00 Chicago | First Round | Cleveland | 3-0 | St. Louis | | |
| 09-Jun-09 - 19:00 New York | First Round | Rochester | 1-1
(0-0) | Pttsburgh | | |
| 09-Jun-09 - 19:05 New York | First Round | Harisburg | 4-1 | Reading | | |
| 09-Jun-09 - 19:05 Chicago | First Round | Minnesota | 3-2 | Nebraska | | |
| 09-Jun-09 - 19:30 New York | First Round | Charlston | 2-0 | Atlanta | | |
| 09-Jun-09 - 19:30 Chicago | First Round | Austin 08 | 2-0 | Brilla | | |
| 09-Jun-09 - 20:00 New York | First Round | Ft. Laud | 2-1 | Lynchs | | |
| 09-Jun-09 - 20:00 Denver | First Round | El Paso | 2-1 | Arizona | | |
| 10-Jun-09 - 19:00 New York | First Round | OceanCity | 3-0 | CP Balt | | |
| 10-Jun-09 - 19:00 New York | First Round | Maryland | 1-0 | Aegean | | |
| 16-Jun-09 - 19:00 New York | Second Round | NC | 3-3
(0-0) | Wilmngton | | |
| 16-Jun-09 - 19:00 New York | Second Round | Rochester | 2-1 | Cleveland | | |
| 16-Jun-09 - 19:00 Los Angeles | Second Round | Sonoma | 0-3 | Portland | | |
| 16-Jun-09 - 19:00 New York | Second Round | OceanCity | 1-0 | Maryland | | |
| 16-Jun-09 - 19:05 New York | Second Round | Harisburg | 0-0
(0-0) | West Mass | | |
| 16-Jun-09 - 19:05 Chicago | Second Round | Minnesota | 4-0 | Fire PDL | | |
| 16-Jun-09 - 19:30 Chicago | Second Round | Austin 08 | 2-0 | El Paso | | |
| 16-Jun-09 - 20:00 New York | Second Round | Ft. Laud | 0-1 | Charlston | | |
| 30-Jun-09 - 19:00 New York | Third Round | N England | 1-2 | Harisburg | | |
| 30-Jun-09 - 19:00 New York | Third Round | Wilmngton | 1-0 | Chicago | | |
| 30-Jun-09 - 19:00 New York | Third Round | Rochester | 1-1
(0-0) | Columbus | | |
| 30-Jun-09 - 19:05 Chicago | Third Round | Minnesota | 3-3
(0-0) | Sprtng KC | | |
| 30-Jun-09 - 19:30 New York | Third Round | DC United | 2-0 | OceanCity | | |
| 30-Jun-09 - 19:30 New York | Third Round | Charlston | 3-1 | Chivas USA | | |
| 01-Jul-09 - 19:00 Los Angeles | Third Round | Portland | 1-2 | Seattle | | |
| 01-Jul-09 - 19:30 Chicago | Third Round | Austin 08 | 0-2 | Harisburg | | |
| 07-Jul-09 - 19:00 New York | Quarter Finals | Rochester | 2-1 | Wilmngton | | |
| 07-Jul-09 - 19:00 Los Angeles | Quarter Finals | Seattle | 1-0 | Sprtng KC | | |
| 07-Jul-09 - 19:30 New York | Quarter Finals | DC United | 2-1 | Harisburg | | |
| 07-Jul-09 - 19:30 New York | Quarter Finals | Charlston | 0-4 | Houston | | |
| 21-Jul-09 - 19:00 Los Angeles | Semi Finals | Seattle | 2-1 | Houston | | |
| 21-Jul-09 - 19:30 New York | Semi Finals | DC United | 2-1 | Rochester | | |
| 02-Sep-09 - 19:30 New York | Final | DC United | 1-2 | Seattle | | |
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