1. Round | 24/04/2021 | Sporting Kansas City | - | Orlando City | 1:1 | ||||
2. Round | 02/05/2021 | Orlando City | - | FC Cincinnati | 3:0 | ||||
2. Round | 17/05/2021 | D.C. United | - | Orlando City | 0:1 | ||||
2. Round | 23/05/2021 | Orlando City | - | Toronto FC | 1:0 | ||||
3. Round | 26/06/2021 | Inter Miami CF | - | Orlando City | 1:2 | ||||
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 | 08/08/2021 | FC Cincinnati | - | Orlando City | 1:1 | ||||
5. Round | 19/08/2021 | Nashville SC | - | Orlando City | 1:1 | ||||
5. Round | 22/08/2021 | Orlando City | - | Chicago Fire | 1:0 | ||||
5. Round | 28/08/2021 | Orlando City | - | Inter Miami CF | 0:0 | ||||
6. Round | 05/09/2021 | Orlando City | - | Columbus Crew | 3:2 | ||||
6. Round | 11/09/2021 | Atlanta United FC | - | Orlando City | 3:0 | ||||
6. Round | 19/09/2021 | Philadelphia Union | - | Orlando City | 3:1 | ||||
7. Round | 25/10/2021 | Orlando City | - | New England Revolution | 2:2 |