3. Round | 06/05/2018 | Saint Louis FC | - | Portland Timbers 2 | 0:0 | ||||
3. Round | 13/05/2018 | Seattle Sounders 2 | - | Portland Timbers 2 | 0:1 | ||||
3. Round | 18/05/2018 | Portland Timbers 2 | - | Los Angeles Galaxy II | 7:3 | ||||
5. Round | 08/07/2018 | Portland Timbers 2 | - | Fresno FC | 2:4 | ||||
6. Round | 05/08/2018 | Portland Timbers 2 | - | Phoenix Rising | 1:4 | ||||
7. Round | 09/09/2018 | Portland Timbers 2 | - | Tulsa Roughnecks | 4:0 |