1. Round | 12/03/2023 | San Antonio FC | - | Oakland Roots | 3:1 | ||||
1. Round | 20/03/2023 | Rio Grande Valley FC | - | Oakland Roots | 1:1 | ||||
2. Round | 02/04/2023 | Oakland Roots | - | New Mexico United | 1:0 | ||||
2. Round | 09/04/2023 | Indy Eleven | - | Oakland Roots | 0:3 | ||||
2. Round | 16/04/2023 | Oakland Roots | - | Hartford Athletic | 1:2 | ||||
2. Round | 30/04/2023 | Oakland Roots | - | Miami FC | 0:0 | ||||
3. Round | 07/05/2023 | Birmingham Legion | - | Oakland Roots | 1:4 | ||||
3. Round | 14/05/2023 | Oakland Roots | - | Orange County SC | 3:0 | ||||
3. Round | 21/05/2023 | Sacramento Republic | - | Oakland Roots | 3:1 | ||||
3. Round | 28/05/2023 | Oakland Roots | - | San Diego Loyal | 2:0 |