| 2. Round | 08/05/2021 | Sporting Kansas City 2 | - | OKC Energy FC | 1:1 |  |
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| 2. Round | 27/05/2021 | Birmingham Legion | - | OKC Energy FC | 1:0 | ||||
| 2. Round | 30/05/2021 | OKC Energy FC | - | Memphis 901 | 0:0 | ||||
| 3. Round | 03/06/2021 | Indy Eleven | - | OKC Energy FC | 1:1 | |
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| 3. Round | 13/06/2021 | OKC Energy FC | - | Birmingham Legion | 1:2 | ||||
| 3. Round | 20/06/2021 | Memphis 901 | - | OKC Energy FC | 0:1 | ||||
| 3. Round | 24/06/2021 | OKC Energy FC | - | Sporting Kansas City 2 | 1:0 | ||||
| 3. Round | 28/06/2021 | Atlanta United II | - | OKC Energy FC | 1:2 | ||||
| 4. Round | 03/07/2021 | OKC Energy FC | - | FC Tulsa | 0:0 | ||||
| 4. Round | 15/07/2021 | Louisville City FC | - | OKC Energy FC | 3:1 | ||||
| 4. Round | 18/07/2021 | FC Tulsa | - | OKC Energy FC | 1:2 | |
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| 4. Round | 25/07/2021 | OKC Energy FC | - | Sporting Kansas City 2 | 0:0 | ||||
| 5. Round | 08/08/2021 | OKC Energy FC | - | Memphis 901 | 4:1 | ||||
| 5. Round | 15/08/2021 | Indy Eleven | - | OKC Energy FC | 2:1 |
Cuba