| 2. Round | 16/05/2021 | New Mexico United | - | Austin Bold | 3:1 | ||||
| 2. Round | 22/05/2021 | Real Monarchs SLC | - | Austin Bold | 1:1 | ||||
| 3. Round | 04/06/2021 | Austin Bold | - | El Paso Locomotive | 0:1 | ||||
| 3. Round | 06/06/2021 | Pittsburgh Riverhounds | - | Austin Bold | 0:1 |  |
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| 3. Round | 17/06/2021 | Rio Grande Valley FC | - | Austin Bold | 1:2 | ||||
| 3. Round | 23/06/2021 | Austin Bold | - | Colorado Springs Switchbacks | 2:3 | ||||
| 3. Round | 27/06/2021 | Oakland Roots | - | Austin Bold | 0:0 | ||||
| 4. Round | 19/07/2021 | Austin Bold | - | Real Monarchs SLC | 1:0 |
Jamaica