2. Round | 31/03/2019 | Orlando City | - | D.C. United | 1:2 | ||||
3. Round | 16/05/2019 | Seattle Sounders | - | Orlando City | 2:1 | ||||
3. Round | 19/05/2019 | Orlando City | - | FC Cincinnati | 5:1 | ||||
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 | ||||
5. Round | 14/07/2019 | Orlando City | - | Columbus Crew | 1:0 | ||||
5. Round | 19/07/2019 | Portland Timbers | - | Orlando City | 1:1 | ||||
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 | 08/09/2019 | Orlando City | - | Los Angeles FC | 2:2 | ||||
7. Round | 15/09/2019 | Orlando City | - | New England Revolution | 3:3 | ||||
7. Round | 29/09/2019 | FC Cincinnati | - | Orlando City | 1:1 | ||||
8. Round | 06/10/2019 | Orlando City | - | Chicago Fire | 2:5 |