1. Round | 02/03/2019 | Orlando City | - | New York City FC | 2:2 | ||||
1. Round | 09/03/2019 | Chicago Fire | - | Orlando City | 1:1 | ||||
2. Round | 14/04/2019 | Real Salt Lake | - | Orlando City | 2:1 | ||||
3. Round | 12/05/2019 | Atlanta United FC | - | Orlando City | 1:0 | ||||
5. Round | 04/07/2019 | Orlando City | - | Philadelphia Union | 1:3 | ||||
5. Round | 07/07/2019 | Philadelphia Union | - | Orlando City | 2:2 | ||||
5. Round | 14/07/2019 | Orlando City | - | Columbus Crew | 1:0 | ||||
5. Round | 19/07/2019 | Portland Timbers | - | Orlando City | 1:1 | ||||
5. Round | 28/07/2019 | New England Revolution | - | Orlando City | 4:1 | ||||
6. Round | 11/08/2019 | Toronto FC | - | Orlando City | 1:1 | ||||
6. Round | 15/08/2019 | Orlando City | - | Sporting Kansas City | 1:0 | ||||
6. Round | 18/08/2019 | Minnesota United FC | - | Orlando City | 1:1 | ||||
6. Round | 24/08/2019 | Orlando City | - | Atlanta United FC | 0:1 | ||||
7. Round | 01/09/2019 | San Jose Earthquakes | - | Orlando City | 3:0 | ||||
7. Round | 22/09/2019 | Houston Dynamo | - | Orlando City | 2:1 | ||||
8. Round | 06/10/2019 | Orlando City | - | Chicago Fire | 2:5 |