| 5. Round | 05/07/2009 | Los Angeles Galaxy | - | New England Revolution | 1:0 | ||||
| 5. Round | 11/07/2009 | New England Revolution | - | Kansas City Wizards | 0:0 | ||||
| 6. Round | 02/08/2009 | New England Revolution | - | Toronto FC | 1:1 |  |
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| 6. Round | 08/08/2009 | New England Revolution | - | Los Angeles Galaxy | 1:2 | ||||
| 6. Round | 21/08/2009 | Seattle Sounders | - | New England Revolution | 0:1 |  |
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| 7. Round | 06/09/2009 | New England Revolution | - | Kansas City Wizards | 2:4 | |
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| 7. Round | 13/09/2009 | CD Chivas | - | New England Revolution | 2:0 |  |
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| 7. Round | 27/09/2009 | New England Revolution | - | Seattle Sounders | 2:1 | ||||
| 8. Round | 17/10/2009 | New England Revolution | - | Chicago Fire | 0:0 | ||||
| 8. Round | 25/10/2009 | Columbus Crew | - | New England Revolution | 0:1 |
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