| 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 | ||||
| 2. Jornada | 08.05.2021 | Chicago Fire | - | Philadelphia Union | 0:2 | ||||
| 2. Jornada | 14.05.2021 | D.C. United | - | Chicago Fire | 1:0 |  |
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| 2. Jornada | 23.05.2021 | Chicago Fire | - | Inter Miami CF | 1:0 | ||||
| 3. Jornada | 27.06.2021 | Chicago Fire | - | Philadelphia Union | 3:3 | ||||
| 4. Jornada | 04.07.2021 | Chicago Fire | - | Atlanta United FC | 3:0 |  |
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| 4. Jornada | 08.07.2021 | Chicago Fire | - | Orlando City | 3:1 | ||||
| 4. Jornada | 18.07.2021 | Nashville SC | - | Chicago Fire | 5:1 | ||||
| 4. Jornada | 22.07.2021 | Chicago Fire | - | D.C. United | 2:2 | ||||
| 4. Jornada | 25.07.2021 | Chicago Fire | - | Toronto FC | 1:2 | ||||
| 5. Jornada | 02.08.2021 | Philadelphia Union | - | Chicago Fire | 1:1 | |
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