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 | 15/09/2019 | Orlando City | - | New England Revolution | 3:3 | ||||
7. Round | 22/09/2019 | Houston Dynamo | - | Orlando City | 2:1 | ||||
7. Round | 29/09/2019 | FC Cincinnati | - | Orlando City | 1:1 | ||||
8. Round | 06/10/2019 | Orlando City | - | Chicago Fire | 2:5 |