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 | 16/03/2019 | Orlando City | - | Impact de Montréal | 1:3 | ||||
3. Round | 16/05/2019 | Seattle Sounders | - | Orlando City | 2:1 | ||||
4. Round | 30/06/2019 | Columbus Crew | - | Orlando City | 0:2 | ||||
5. Round | 04/07/2019 | Orlando City | - | Philadelphia Union | 1:3 | ||||
5. Round | 07/07/2019 | Philadelphia Union | - | Orlando City | 2:2 | ||||
5. Round | 19/07/2019 | Portland Timbers | - | Orlando City | 1:1 |