| 1. Round | 10/03/2019 | Tulsa Roughnecks | - | Portland Timbers 2 | 1:1 | ||||
| 1. Round | 17/03/2019 | San Antonio FC | - | Portland Timbers 2 | 1:3 |  |
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| 1. Round | 24/03/2019 | Portland Timbers 2 | - | Las Vegas Lights FC | 3:1 | ||||
| 3. Round | 12/05/2019 | Tacoma Defiance | - | Portland Timbers 2 | 1:4 | ||||
| 3. Round | 26/05/2019 | Portland Timbers 2 | - | El Paso Locomotive | 1:1 | ||||
| 3. Round | 30/05/2019 | Portland Timbers 2 | - | Real Monarchs SLC | 2:1 | ||||
| 4. Round | 09/06/2019 | Austin Bold | - | Portland Timbers 2 | 2:2 | ||||
| 4. Round | 16/06/2019 | Portland Timbers 2 | - | Fresno FC | 2:2 | ||||
| 5. Round | 29/07/2019 | Portland Timbers 2 | - | Los Angeles Galaxy II | 1:2 |
Costa Rica