1. Round | 08/03/2020 | Phoenix Rising | - | Portland Timbers 2 | 6:1 | ||||
2. Round | 19/07/2020 | Tacoma Defiance | - | Portland Timbers 2 | 3:0 | ||||
2. Round | 30/07/2020 | Portland Timbers 2 | - | Reno 1868 FC | 1:4 | ||||
3. Round | 04/08/2020 | Portland Timbers 2 | - | Tacoma Defiance | 0:4 | ||||
3. Round | 09/08/2020 | Portland Timbers 2 | - | Sacramento Republic | 0:1 | ||||
4. Round | 25/09/2020 | Portland Timbers 2 | - | Tacoma Defiance | 3:1 | ||||
4. Round | 27/09/2020 | Tacoma Defiance | - | Portland Timbers 2 | 2:1 | ||||
5. Round | 04/10/2020 | Sacramento Republic | - | Portland Timbers 2 | 4:0 |