3. Round | 29/05/2016 | Chicago Fire | - | Portland Timbers | 1:1 | ||||
4. Round | 19/06/2016 | Colorado Rapids | - | Chicago Fire | 2:1 | ||||
4. Round | 23/06/2016 | Philadelphia Union | - | Chicago Fire | 4:3 | ||||
6. Round | 07/08/2016 | Real Salt Lake | - | Chicago Fire | 3:1 | ||||
6. Round | 14/08/2016 | Chicago Fire | - | Orlando City | 2:2 |