| 1. Jornada | 02.03.2019 | Orlando City | - | New York City FC | 2:2 | ||||
| 1. Jornada | 09.03.2019 | Chicago Fire | - | Orlando City | 1:1 | ||||
| 2. Jornada | 14.04.2019 | Real Salt Lake | - | Orlando City | 2:1 | ||||
| 3. Jornada | 12.05.2019 | Atlanta United FC | - | Orlando City | 1:0 | ||||
| 5. Jornada | 04.07.2019 | Orlando City | - | Philadelphia Union | 1:3 | ||||
| 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 | 19.07.2019 | Portland Timbers | - | Orlando City | 1:1 | ||||
| 5. Jornada | 28.07.2019 | New England Revolution | - | Orlando City | 4:1 | ||||
| 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 | 22.09.2019 | Houston Dynamo | - | Orlando City | 2:1 | ||||
| 8. Jornada | 06.10.2019 | Orlando City | - | Chicago Fire | 2:5 |
Canadá
Jamaica