1. Round | 17/03/2019 | San Antonio FC | - | Portland Timbers 2 | 1:3 | ||||
1. Round | 24/03/2019 | Portland Timbers 2 | - | Las Vegas Lights FC | 3:1 | ||||
1. Round | 31/03/2019 | Los Angeles Galaxy II | - | Portland Timbers 2 | 3:2 | ||||
3. Round | 01/05/2019 | Portland Timbers 2 | - | Rio Grande Valley FC | 1:2 | ||||
3. Round | 30/05/2019 | Portland Timbers 2 | - | Real Monarchs SLC | 2:1 | ||||
4. Round | 16/06/2019 | Portland Timbers 2 | - | Fresno FC | 2:2 | ||||
4. Round | 23/06/2019 | Orange County SC | - | Portland Timbers 2 | 0:2 | ||||
4. Round | 27/06/2019 | Portland Timbers 2 | - | Reno 1868 FC | 1:2 | ||||
4. Round | 30/06/2019 | Phoenix Rising | - | Portland Timbers 2 | 4:2 | ||||
5. Round | 07/07/2019 | Portland Timbers 2 | - | Tulsa Roughnecks | 1:1 | ||||
5. Round | 14/07/2019 | Sacramento Republic | - | Portland Timbers 2 | 1:0 | ||||
5. Round | 21/07/2019 | Fresno FC | - | Portland Timbers 2 | 2:1 | ||||
5. Round | 29/07/2019 | Portland Timbers 2 | - | Los Angeles Galaxy II | 1:2 |