3. Round | 23/06/2021 | Orlando City | - | San Jose Earthquakes | 5:0 | ||||
3. Round | 26/06/2021 | Inter Miami CF | - | Orlando City | 1:2 | ||||
4. Round | 04/07/2021 | Orlando City | - | New York RB | 1:2 | ||||
4. Round | 08/07/2021 | Chicago Fire | - | Orlando City | 3:1 | ||||
4. Round | 18/07/2021 | Toronto FC | - | Orlando City | 1:1 | ||||
4. Round | 23/07/2021 | Orlando City | - | Philadelphia Union | 2:1 | ||||
4. Round | 25/07/2021 | New York City FC | - | Orlando City | 5:0 | ||||
4. Round | 31/07/2021 | Orlando City | - | Atlanta United FC | 3:2 | ||||
5. Round | 05/08/2021 | Orlando City | - | Inter Miami CF | 1:1 | ||||
5. Round | 08/08/2021 | FC Cincinnati | - | Orlando City | 1:1 | ||||
6. Round | 11/09/2021 | Atlanta United FC | - | Orlando City | 3:0 | ||||
7. Round | 17/10/2021 | FC Cincinnati | - | Orlando City | 0:1 | ||||
7. Round | 21/10/2021 | Orlando City | - | CF Montréal | 1:1 | ||||
8. Round | 07/11/2021 | CF Montréal | - | Orlando City | 0:2 |