| 1. Round | 09/03/2019 | Reno 1868 FC | - | Orange County SC | 2:2 | ||||
| 1. Round | 17/03/2019 | Orange County SC | - | Tulsa Roughnecks | 3:5 | ||||
| 1. Round | 24/03/2019 | Orange County SC | - | New Mexico United | 2:2 | ||||
| 4. Round | 16/06/2019 | Phoenix Rising | - | Orange County SC | 3:0 | ||||
| 4. Round | 23/06/2019 | Orange County SC | - | Portland Timbers 2 | 0:2 | ||||
| 7. Round | 29/09/2019 | Rio Grande Valley FC | - | Orange County SC | 2:0 |
Japan