1. Round | 02/03/2019 | Orlando City | - | New York City FC | 2:2 | ||||
1. Round | 09/03/2019 | Chicago Fire | - | Orlando City | 1:1 | ||||
1. Round | 23/03/2019 | New York RB | - | Orlando City | 0:1 | ||||
3. Round | 12/05/2019 | Atlanta United FC | - | Orlando City | 1:0 | ||||
5. Round | 07/07/2019 | Philadelphia Union | - | Orlando City | 2:2 | ||||
5. Round | 19/07/2019 | Portland Timbers | - | Orlando City | 1:1 |