1. Round | 09/03/2014 | CD Chivas | - | Chicago Fire | 3:2 | ||||
2. Round | 05/04/2014 | Chicago Fire | - | Philadelphia Union | 2:2 | ||||
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 | ||||
5. Round | 06/07/2014 | Sporting Kansas City | - | Chicago Fire | 1:1 |