| 1. Jornada | 16.03.2019 | Orlando City | - | Impact de Montréal | 1:3 | ||||
| 1. Jornada | 24.03.2019 | New York RB | - | Orlando City | 0:1 | ||||
| 2. Jornada | 01.04.2019 | Orlando City | - | D.C. United | 1:2 | ||||
| 2. Jornada | 07.04.2019 | Orlando City | - | Colorado Rapids | 4:3 | ||||
| 4. Jornada | 27.06.2019 | D.C. United | - | Orlando City | 1:0 | ||||
| 4. Jornada | 30.06.2019 | Columbus Crew | - | Orlando City | 0:2 |  |
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| 5. Jornada | 07.07.2019 | Philadelphia Union | - | Orlando City | 2:2 | ||||
| 5. Jornada | 14.07.2019 | Orlando City | - | Columbus Crew | 1:0 | |
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| 5. Jornada | 22.07.2019 | Orlando City | - | New York RB | 0:1 | ||||
| 6. Jornada | 04.08.2019 | Orlando City | - | FC Dallas | 2:0 |  |
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| 6. Jornada | 11.08.2019 | Toronto FC | - | Orlando City | 1:1 | ||||
| 6. Jornada | 15.08.2019 | Orlando City | - | Sporting Kansas City | 1:0 | ||||
| 6. Jornada | 18.08.2019 | Minnesota United FC | - | Orlando City | 1:1 | ||||
| 6. Jornada | 24.08.2019 | Orlando City | - | Atlanta United FC | 0:1 | ||||
| 7. Jornada | 01.09.2019 | San Jose Earthquakes | - | Orlando City | 3:0 | ||||
| 7. Jornada | 15.09.2019 | Orlando City | - | New England Revolution | 3:3 | ||||
| 7. Jornada | 22.09.2019 | Houston Dynamo | - | Orlando City | 2:1 |
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