1. Round | 24/04/2021 | Sporting Kansas City | - | Orlando City | 1:1 | ||||
2. Round | 23/05/2021 | Orlando City | - | Toronto FC | 1:0 | ||||
3. Round | 23/06/2021 | Orlando City | - | San Jose Earthquakes | 5:0 | ||||
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 | ||||
5. Round | 28/08/2021 | Orlando City | - | Inter Miami CF | 0:0 | ||||
6. Round | 16/09/2021 | Orlando City | - | CF Montréal | 2:4 | ||||
6. Round | 30/09/2021 | Nashville SC | - | Orlando City | 2:2 |