| 3. Round | 27/05/2018 | Orlando City | - | Chicago Fire | 1:2 | ||||
| 3. Round | 31/05/2018 | Philadelphia Union | - | Chicago Fire | 3:1 | ||||
| 4. Round | 03/06/2018 | Chicago Fire | - | San Jose Earthquakes | 2:1 | ||||
| 8. Round | 21/10/2018 | Atlanta United FC | - | Chicago Fire | 2:1 | ||||
| 8. Round | 28/10/2018 | Chicago Fire | - | D.C. United | 0:0 |
USA