| 1. Round | 28/03/2009 | D.C. United | - | Chicago Fire | 1:1 | ||||
| 2. Round | 11/04/2009 | San Jose Earthquakes | - | Chicago Fire | 3:3 |  |
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| 3. Round | 16/05/2009 | Toronto FC | - | Chicago Fire | 0:2 | ||||
| 4. Round | 06/06/2009 | Chicago Fire | - | Houston Dynamo | 0:1 | ||||
| 5. Round | 19/07/2009 | Chicago Fire | - | San Jose Earthquakes | 2:0 | ||||
| 6. Round | 10/08/2009 | Houston Dynamo | - | Chicago Fire | 3:2 | ||||
| 6. Round | 16/08/2009 | Kansas City Wizards | - | Chicago Fire | 0:2 | ||||
| 6. Round | 20/08/2009 | Chicago Fire | - | Los Angeles Galaxy | 0:2 | ||||
| 6. Round | 23/08/2009 | Chicago Fire | - | Colorado Rapids | 3:2 |  |
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| 7. Round | 13/09/2009 | Real Salt Lake | - | Chicago Fire | 1:1 | ||||
| 8. Round | 17/10/2009 | New England Revolution | - | Chicago Fire | 0:0 | ||||
| 8. Round | 23/10/2009 | Chicago Fire | - | CD Chivas | 1:0 |
USA