3. Round | 16/08/2020 | Reno 1868 FC | - | Portland Timbers 2 | 5:2 | ||||
3. Round | 23/08/2020 | Sacramento Republic | - | Portland Timbers 2 | 2:1 | ||||
3. Round | 27/08/2020 | Portland Timbers 2 | - | Los Angeles Galaxy II | 2:3 | ||||
4. Round | 27/09/2020 | Tacoma Defiance | - | Portland Timbers 2 | 2:1 | ||||
5. Round | 04/10/2020 | Sacramento Republic | - | Portland Timbers 2 | 4:0 |