| 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 | ||||
| 2. Jornada | 14.04.2019 | Real Salt Lake | - | Orlando City | 2:1 | ||||
| 2. Jornada | 20.04.2019 | Orlando City | - | Vancouver Whitecaps | 1:0 | ||||
| 2. Jornada | 27.04.2019 | New York City FC | - | Orlando City | 1:1 | ||||
| 3. Jornada | 04.05.2019 | Orlando City | - | Toronto FC | 0:2 | ||||
| 3. Jornada | 12.05.2019 | Atlanta United FC | - | Orlando City | 1:0 | ||||
| 3. Jornada | 16.05.2019 | Seattle Sounders | - | Orlando City | 2:1 | ||||
| 3. Jornada | 19.05.2019 | Orlando City | - | FC Cincinnati | 5:1 | ||||
| 3. Jornada | 25.05.2019 | Orlando City | - | Los Angeles Galaxy | 0:1 | ||||
| 4. Jornada | 01.06.2019 | Impact de Montréal | - | Orlando City | 0:3 |  |
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| 5. Jornada | 22.07.2019 | Orlando City | - | New York RB | 0:1 | ||||
| 5. Jornada | 28.07.2019 | New England Revolution | - | Orlando City | 4:1 | ||||
| 6. Jornada | 04.08.2019 | Orlando City | - | FC Dallas | 2:0 | ||||
| 7. Jornada | 29.09.2019 | FC Cincinnati | - | Orlando City | 1:1 |
Portugal