| 1. Jornada | 09.03.2019 | Chicago Fire | - | Orlando City | 1:1 | ||||
| 1. Jornada | 16.03.2019 | Chicago Fire | - | Seattle Sounders | 2:4 |  |
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| 3. Jornada | 25.05.2019 | Chicago Fire | - | New York City FC | 1:1 | ||||
| 3. Jornada | 30.05.2019 | D.C. United | - | Chicago Fire | 3:3 | ||||
| 4. Jornada | 02.06.2019 | Atlanta United FC | - | Chicago Fire | 2:0 | ||||
| 4. Jornada | 23.06.2019 | Chicago Fire | - | Real Salt Lake | 1:1 | ||||
| 4. Jornada | 29.06.2019 | New York RB | - | Chicago Fire | 3:1 | ||||
| 5. Jornada | 04.07.2019 | Chicago Fire | - | Atlanta United FC | 5:1 | |
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| 5. Jornada | 07.07.2019 | Sporting Kansas City | - | Chicago Fire | 1:0 | |
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| 5. Jornada | 14.07.2019 | Chicago Fire | - | FC Cincinnati | 1:2 | ||||
| 5. Jornada | 18.07.2019 | Chicago Fire | - | Columbus Crew | 2:2 | ||||
| 5. Jornada | 21.07.2019 | Philadelphia Union | - | Chicago Fire | 2:0 | ||||
| 6. Jornada | 25.08.2019 | New England Revolution | - | Chicago Fire | 2:1 | ||||
| 7. Jornada | 01.09.2019 | Columbus Crew | - | Chicago Fire | 1:1 | ||||
| 7. Jornada | 22.09.2019 | FC Cincinnati | - | Chicago Fire | 0:0 | ||||
| 7. Jornada | 29.09.2019 | Chicago Fire | - | Toronto FC | 2:2 | |
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| 8. Jornada | 06.10.2019 | Orlando City | - | Chicago Fire | 2:5 | |
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