2. Round | 05/03/2023 | Orlando City | - | FC Cincinnati | 0:0 | ||||
2. Round | 12/03/2023 | D.C. United | - | Orlando City | 1:1 | ||||
2. Round | 18/03/2023 | Orlando City | - | Charlotte FC | 1:2 | ||||
2. Round | 25/03/2023 | Philadelphia Union | - | Orlando City | 1:2 | ||||
3. Round | 02/04/2023 | Orlando City | - | Nashville SC | 0:2 | ||||
3. Round | 16/04/2023 | Minnesota United FC | - | Orlando City | 1:2 | ||||
3. Round | 23/04/2023 | Orlando City | - | D.C. United | 1:3 | ||||
3. Round | 30/04/2023 | Orlando City | - | Los Angeles Galaxy | 2:0 | ||||
4. Round | 07/05/2023 | CF Montréal | - | Orlando City | 2:0 | ||||
4. Round | 14/05/2023 | Columbus Crew | - | Orlando City | 2:2 | ||||
4. Round | 18/05/2023 | Orlando City | - | New York City FC | 1:1 | ||||
4. Round | 21/05/2023 | Inter Miami CF | - | Orlando City | 1:3 | ||||
5. Round | 22/06/2023 | Orlando City | - | Philadelphia Union | 2:2 | ||||
8. Round | 21/09/2023 | New York City FC | - | Orlando City | 2:0 | ||||
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 | 08/10/2023 | Orlando City | - | New England Revolution | 3:2 | ||||
9. Round | 21/10/2023 | Toronto FC | - | Orlando City | 0:2 |