7. Round | 21/08/2023 | Chicago Fire | - | Orlando City | 1:3 | ||||
7. Round | 27/08/2023 | Orlando City | - | St. Louis City SC | 2:1 | ||||
7. Round | 31/08/2023 | Charlotte FC | - | Orlando City | 1:1 | ||||
8. Round | 03/09/2023 | FC Cincinnati | - | Orlando City | 0:1 | ||||
8. Round | 25/09/2023 | Orlando City | - | Inter Miami CF | 1:1 | ||||
8. Round | 01/10/2023 | Orlando City | - | CF Montréal | 3:0 | ||||
9. Round | 05/10/2023 | Nashville SC | - | Orlando City | 0:1 | ||||
9. Round | 08/10/2023 | Orlando City | - | New England Revolution | 3:2 | ||||
9. Round | 21/10/2023 | Toronto FC | - | Orlando City | 0:2 |