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 | ||||
5. Round | 29/07/2019 | Portland Timbers 2 | - | Los Angeles Galaxy II | 1:2 | ||||
7. Round | 14/09/2019 | Real Monarchs SLC | - | Portland Timbers 2 | 5:1 |