| 1. Jornada | 03.03.2019 | Los Angeles Galaxy | - | Chicago Fire | 2:1 | ||||
| 1. Jornada | 09.03.2019 | Chicago Fire | - | Orlando City | 1:1 |  |
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| 2. Jornada | 25.04.2019 | New York City FC | - | Chicago Fire | 1:0 | ||||
| 2. Jornada | 28.04.2019 | Impact de Montréal | - | Chicago Fire | 1:0 | ||||
| 3. Jornada | 05.05.2019 | Los Angeles FC | - | Chicago Fire | 0:0 |  |
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| 3. Jornada | 09.05.2019 | Chicago Fire | - | New England Revolution | 5:0 | ||||
| 3. Jornada | 12.05.2019 | Chicago Fire | - | Minnesota United FC | 2:0 | ||||
| 3. Jornada | 18.05.2019 | San Jose Earthquakes | - | Chicago Fire | 4:1 | |
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| 4. Jornada | 02.06.2019 | Atlanta United FC | - | Chicago Fire | 2:0 | |
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| 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 | ||||
| 5. Jornada | 14.07.2019 | Chicago Fire | - | FC Cincinnati | 1:2 | |
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| 5. Jornada | 18.07.2019 | Chicago Fire | - | Columbus Crew | 2:2 | ||||
| 5. Jornada | 21.07.2019 | Philadelphia Union | - | Chicago Fire | 2:0 |
Cuba