[7] Oakland Roots 2-0 San Diego Loyal [3] 2023-05-28 02:00
Stadium: Laney College Football Stadium Round: 1
Head to Head
| USA USL Championship | 2022/10/24 02:00 | San Diego Loyal v Oakland Roots | W | 0-3 |
| USA USL Championship | 2022/08/25 02:00 | San Diego Loyal v Oakland Roots | W | 1-3 |
| USA USL Championship | 2022/04/14 02:00 | Oakland Roots v San Diego Loyal | D | 2-2 |
| USA USL Championship | 2021/10/24 22:00 | San Diego Loyal v Oakland Roots | W | 3-4 |
| USA USL Championship | 2021/09/23 02:00 | Oakland Roots v San Diego Loyal | W | 2-1 |
| USA USL Championship | 2021/09/12 02:00 | Oakland Roots v San Diego Loyal | D | 0-0 |
| USA USL Championship | 2021/06/30 02:30 | San Diego Loyal v Oakland Roots | L | 1-0 |
Home History
| USA USL Championship | 2023/05/21 02:00 | Sacramento Republic v Oakland Roots | L | 3-1 |
| USA USL Championship | 2023/05/14 03:00 | Oakland Roots v Orange County SC | W | 3-0 |
| USA USL Championship | 2023/05/06 23:30 | Birmingham Legion FC v Oakland Roots | W | 1-4 |
| USA USL Championship | 2023/04/30 02:00 | Oakland Roots v Miami FC | D | 0-0 |
| USA US Open Cup | 2023/04/27 02:00 | Sacramento Republic v Oakland Roots | L | 1-0 |
| USA USL Championship | 2023/04/23 20:00 | Loudoun United FC v Oakland Roots | L | 2-0 |
| USA USL Championship | 2023/04/16 02:00 | Oakland Roots v Hartford Athletic | L | 1-2 |
| USA USL Championship | 2023/04/08 23:00 | Indy Eleven v Oakland Roots | W | 0-3 |
Away History
| USA USL Championship | 2023/05/20 23:00 | Miami FC v San Diego Loyal | W | 2-3 |
| USA USL Championship | 2023/05/14 02:00 | San Diego Loyal v Rio Grande Valley FC Toros | L | 2-3 |
| USA USL Championship | 2023/05/07 02:00 | Orange County SC v San Diego Loyal | W | 1-2 |
| USA USL Championship | 2023/04/30 02:00 | San Diego Loyal v El Paso Locomotive FC | L | 1-2 |
| USA US Open Cup | 2023/04/27 02:00 | Seattle Sounders v San Diego Loyal | D | 3-3 |
| USA USL Championship | 2023/04/23 22:00 | San Diego Loyal v Tampa Bay Rowdies | W | 1-0 |
| USA USL Championship | 2023/04/16 01:00 | New Mexico United v San Diego Loyal | D | 1-1 |
| USA USL Championship | 2023/04/08 21:00 | San Diego Loyal v Tulsa | W | 2-1 |