| 1. Round | 16/03/2019 | Orlando City | - | Impact de Montréal | 1:3 | ||||
| 1. Round | 23/03/2019 | New York RB | - | Orlando City | 0:1 | ||||
| 3. Round | 16/05/2019 | Seattle Sounders | - | Orlando City | 2:1 | ||||
| 4. Round | 27/06/2019 | D.C. United | - | Orlando City | 1:0 | ||||
| 4. Round | 30/06/2019 | Columbus Crew | - | Orlando City | 0:2 | ||||
| 5. Round | 07/07/2019 | Philadelphia Union | - | Orlando City | 2:2 |  |
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| 5. Round | 14/07/2019 | Orlando City | - | Columbus Crew | 1:0 | ||||
| 5. Round | 19/07/2019 | Portland Timbers | - | Orlando City | 1:1 | |
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| 5. Round | 22/07/2019 | Orlando City | - | New York RB | 0:1 | ||||
| 7. Round | 08/09/2019 | Orlando City | - | Los Angeles FC | 2:2 | ||||
| 7. Round | 15/09/2019 | Orlando City | - | New England Revolution | 3:3 |
Colombia
USA