4. Round | 03/06/2018 | San Antonio FC | - | Portland Timbers 2 | 2:1 | ||||
4. Round | 10/06/2018 | Rio Grande Valley FC | - | Portland Timbers 2 | 0:1 | ||||
6. Round | 12/08/2018 | Swope Park Rangers | - | Portland Timbers 2 | 0:2 | ||||
6. Round | 16/08/2018 | Portland Timbers 2 | - | San Antonio FC | 2:1 | ||||
6. Round | 20/08/2018 | Portland Timbers 2 | - | Seattle Sounders 2 | 4:1 | ||||
6. Round | 23/08/2018 | Portland Timbers 2 | - | Orange County SC | 2:3 | ||||
7. Round | 02/09/2018 | Portland Timbers 2 | - | Saint Louis FC | 1:0 | ||||
8. Round | 14/10/2018 | Phoenix Rising | - | Portland Timbers 2 | 0:1 |