| 1. Round | 16/03/2019 | Orlando City | - | Impact de Montréal | 1:3 |  |
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| 3. Round | 12/05/2019 | Atlanta United FC | - | Orlando City | 1:0 | ||||
| 3. Round | 19/05/2019 | Orlando City | - | FC Cincinnati | 5:1 | ||||
| 3. Round | 25/05/2019 | Orlando City | - | Los Angeles Galaxy | 0:1 | ||||
| 4. Round | 01/06/2019 | Impact de Montréal | - | Orlando City | 0:3 | ||||
| 7. Round | 01/09/2019 | San Jose Earthquakes | - | Orlando City | 3:0 | |
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| 7. Round | 08/09/2019 | Orlando City | - | Los Angeles FC | 2:2 | |
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| 7. Round | 15/09/2019 | Orlando City | - | New England Revolution | 3:3 | |
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| 7. Round | 22/09/2019 | Houston Dynamo | - | Orlando City | 2:1 | |
Colombia