2. Round | 01/03/2020 | Seattle Sounders | - | Chicago Fire | 2:1 | ||||
3. Round | 30/08/2020 | New York City FC | - | Chicago Fire | 3:1 | ||||
4. Round | 20/09/2020 | Orlando City | - | Chicago Fire | 4:1 | ||||
4. Round | 24/09/2020 | Chicago Fire | - | Houston Dynamo | 4:0 | ||||
5. Round | 08/10/2020 | Sporting Kansas City | - | Chicago Fire | 1:0 | ||||
5. Round | 12/10/2020 | Chicago Fire | - | D.C. United | 2:1 |