| 1. Round | 09/03/2014 | CD Chivas | - | Chicago Fire | 3:2 | ||||
| 1. Round | 16/03/2014 | Portland Timbers | - | Chicago Fire | 1:1 | ||||
| 1. Round | 23/03/2014 | Chicago Fire | - | New York RB | 1:1 | ||||
| 1. Round | 29/03/2014 | D.C. United | - | Chicago Fire | 2:2 | ||||
| 2. Round | 05/04/2014 | Chicago Fire | - | Philadelphia Union | 2:2 |  |
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| 2. Round | 12/04/2014 | Impact de Montréal | - | Chicago Fire | 1:1 | ||||
| 2. Round | 19/04/2014 | Chicago Fire | - | New England Revolution | 1:1 | ||||
| 3. Round | 04/05/2014 | Chicago Fire | - | Real Salt Lake | 2:3 | |
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| 3. Round | 11/05/2014 | New York RB | - | Chicago Fire | 4:5 | ||||
| 3. Round | 18/05/2014 | Chicago Fire | - | Sporting Kansas City | 2:1 | ||||
| 3. Round | 25/05/2014 | Columbus Crew | - | Chicago Fire | 2:0 | ||||
| 4. Round | 01/06/2014 | Chicago Fire | - | Los Angeles Galaxy | 1:1 | ||||
| 4. Round | 05/06/2014 | Colorado Rapids | - | Chicago Fire | 0:0 | ||||
| 4. Round | 08/06/2014 | Chicago Fire | - | Seattle Sounders | 2:3 | ||||
| 5. Round | 03/07/2014 | Chicago Fire | - | Toronto FC | 1:1 |
Ecuador