| 5. Jornada | 19.07.2009 | Chicago Fire | - | San Jose Earthquakes | 2:0 | ||||
| 6. Jornada | 10.08.2009 | Houston Dynamo | - | Chicago Fire | 3:2 |  |
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| 6. Jornada | 16.08.2009 | Kansas City Wizards | - | Chicago Fire | 0:2 | ||||
| 6. Jornada | 24.08.2009 | Chicago Fire | - | Colorado Rapids | 3:2 | ||||
| 6. Jornada | 30.08.2009 | Chicago Fire | - | D.C. United | 0:1 | ||||
| 7. Jornada | 13.09.2009 | Real Salt Lake | - | Chicago Fire | 1:1 |  |
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| 7. Jornada | 20.09.2009 | Chicago Fire | - | Columbus Crew | 2:2 | |
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| 7. Jornada | 27.09.2009 | Chicago Fire | - | Toronto FC | 2:2 | ||||
| 8. Jornada | 03.10.2009 | Los Angeles Galaxy | - | Chicago Fire | 1:0 |
Estados Unidos