2. Round | 01/05/2021 | New York RB | - | Chicago Fire | 2:0 | ||||
2. Round | 14/05/2021 | D.C. United | - | Chicago Fire | 1:0 | ||||
2. Round | 22/05/2021 | Chicago Fire | - | Inter Miami CF | 1:0 | ||||
2. Round | 29/05/2021 | Chicago Fire | - | CF Montréal | 0:1 | ||||
3. Round | 20/06/2021 | Columbus Crew | - | Chicago Fire | 2:0 | ||||
3. Round | 24/06/2021 | Chicago Fire | - | FC Cincinnati | 0:1 | ||||
4. Round | 04/07/2021 | Chicago Fire | - | Atlanta United FC | 3:0 | ||||
4. Round | 22/07/2021 | Chicago Fire | - | D.C. United | 2:2 | ||||
5. Round | 05/08/2021 | Chicago Fire | - | New York City FC | 0:0 | ||||
5. Round | 15/08/2021 | Chicago Fire | - | Columbus Crew | 1:0 | ||||
5. Round | 22/08/2021 | Orlando City | - | Chicago Fire | 1:0 | ||||
5. Round | 28/08/2021 | New York RB | - | Chicago Fire | 0:1 | ||||
7. Round | 17/10/2021 | New England Revolution | - | Chicago Fire | 2:2 | ||||
7. Round | 21/10/2021 | FC Cincinnati | - | Chicago Fire | 3:4 | ||||
7. Round | 24/10/2021 | Chicago Fire | - | Real Salt Lake | 1:0 | ||||
7. Round | 28/10/2021 | New York City FC | - | Chicago Fire | 1:0 | ||||
8. Round | 07/11/2021 | Columbus Crew | - | Chicago Fire | 2:0 |