| 1. Jornada | 18.04.2021 | Chicago Fire | - | New England Revolution | 2:2 | ||||
| 1. Jornada | 25.04.2021 | Atlanta United FC | - | Chicago Fire | 3:1 | ||||
| 2. Jornada | 01.05.2021 | New York RB | - | Chicago Fire | 2:0 |  |
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| 2. Jornada | 08.05.2021 | Chicago Fire | - | Philadelphia Union | 0:2 | ||||
| 2. Jornada | 14.05.2021 | D.C. United | - | Chicago Fire | 1:0 | ||||
| 2. Jornada | 23.05.2021 | Chicago Fire | - | Inter Miami CF | 1:0 | ||||
| 2. Jornada | 29.05.2021 | Chicago Fire | - | CF Montréal | 0:1 | ||||
| 3. Jornada | 20.06.2021 | Columbus Crew | - | Chicago Fire | 2:0 | ||||
| 3. Jornada | 24.06.2021 | Chicago Fire | - | FC Cincinnati | 0:1 | ||||
| 3. Jornada | 27.06.2021 | Chicago Fire | - | Philadelphia Union | 3:3 | ||||
| 5. Jornada | 02.08.2021 | Philadelphia Union | - | Chicago Fire | 1:1 | ||||
| 5. Jornada | 05.08.2021 | Chicago Fire | - | New York City FC | 0:0 | ||||
| 5. Jornada | 09.08.2021 | Chicago Fire | - | New York RB | 2:1 | ||||
| 5. Jornada | 16.08.2021 | Chicago Fire | - | Columbus Crew | 1:0 | ||||
| 5. Jornada | 19.08.2021 | Inter Miami CF | - | Chicago Fire | 3:2 |  |
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| 5. Jornada | 22.08.2021 | Orlando City | - | Chicago Fire | 1:0 | ||||
| 7. Jornada | 03.10.2021 | Toronto FC | - | Chicago Fire | 3:1 |
Costa Rica