3. Round | 21/08/2020 | Columbus Crew | - | Chicago Fire | 3:0 | ||||
3. Round | 26/08/2020 | Chicago Fire | - | FC Cincinnati | 3:0 | ||||
3. Round | 30/08/2020 | New York City FC | - | Chicago Fire | 3:1 | ||||
4. Round | 07/09/2020 | Chicago Fire | - | New England Revolution | 1:2 | ||||
4. Round | 20/09/2020 | Orlando City | - | Chicago Fire | 4:1 | ||||
5. Round | 17/10/2020 | Chicago Fire | - | Sporting Kansas City | 2:2 |