| 3. Round | 01/05/2011 | Colorado Rapids | - | Chicago Fire | 1:1 | ||||
| 3. Round | 08/05/2011 | Chicago Fire | - | Vancouver Whitecaps | 0:0 | ||||
| 3. Round | 15/05/2011 | Toronto FC | - | Chicago Fire | 2:2 | ||||
| 3. Round | 22/05/2011 | Philadelphia Union | - | Chicago Fire | 2:1 | ||||
| 4. Round | 05/06/2011 | Chicago Fire | - | Seattle Sounders | 0:0 | ||||
| 4. Round | 10/06/2011 | Sporting Kansas City | - | Chicago Fire | 0:0 | ||||
| 4. Round | 23/06/2011 | Chicago Fire | - | Real Salt Lake | 0:0 | ||||
| 4. Round | 26/06/2011 | Chicago Fire | - | New York RB | 1:1 | ||||
| 7. Round | 29/09/2011 | Real Salt Lake | - | Chicago Fire | 0:3 | ||||
| 8. Round | 01/10/2011 | Houston Dynamo | - | Chicago Fire | 1:1 |
USA