| 5. Round | 19/07/2009 | Chicago Fire | - | San Jose Earthquakes | 2:0 | ||||
| 6. Round | 10/08/2009 | Houston Dynamo | - | Chicago Fire | 3:2 |  |
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| 6. Round | 16/08/2009 | Kansas City Wizards | - | Chicago Fire | 0:2 | ||||
| 6. Round | 23/08/2009 | Chicago Fire | - | Colorado Rapids | 3:2 | ||||
| 6. Round | 30/08/2009 | Chicago Fire | - | D.C. United | 0:1 | ||||
| 7. Round | 13/09/2009 | Real Salt Lake | - | Chicago Fire | 1:1 |  |
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| 7. Round | 20/09/2009 | Chicago Fire | - | Columbus Crew | 2:2 | |
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| 7. Round | 27/09/2009 | Chicago Fire | - | Toronto FC | 2:2 | ||||
| 8. Round | 03/10/2009 | Los Angeles Galaxy | - | Chicago Fire | 1:0 |
USA