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 | 23/04/2023 | Loudoun United | - | Oakland Roots | 2:0 | ||||
2. Round | 30/04/2023 | Oakland Roots | - | Miami FC | 0:0 | ||||
6. Round | 20/08/2023 | Oakland Roots | - | Colorado Springs Switchbacks | 2:3 | ||||
6. Round | 24/08/2023 | New Mexico United | - | Oakland Roots | 1:2 | ||||
6. Round | 27/08/2023 | Louisville City FC | - | Oakland Roots | 2:1 | ||||
7. Round | 03/09/2023 | Oakland Roots | - | Sacramento Republic | 0:1 | ||||
7. Round | 10/09/2023 | Las Vegas Lights FC | - | Oakland Roots | 3:1 | ||||
7. Round | 17/09/2023 | Oakland Roots | - | FC Tulsa | 0:1 | ||||
7. Round | 24/09/2023 | Oakland Roots | - | Monterey Bay FC | 2:2 | ||||
7. Round | 01/10/2023 | Oakland Roots | - | San Antonio FC | 2:2 | ||||
8. Round | 08/10/2023 | San Diego Loyal | - | Oakland Roots | 4:2 | ||||
8. Round | 15/10/2023 | Oakland Roots | - | El Paso Locomotive | 1:2 |