| 1. Round | 08/03/2020 | Phoenix Rising | - | Portland Timbers 2 | 6:1 | ||||
| 2. Round | 19/07/2020 | Tacoma Defiance | - | Portland Timbers 2 | 3:0 |  |
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| 2. Round | 30/07/2020 | Portland Timbers 2 | - | Reno 1868 FC | 1:4 |  |
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| 3. Round | 09/08/2020 | Portland Timbers 2 | - | Sacramento Republic | 0:1 | ||||
| 3. Round | 16/08/2020 | Reno 1868 FC | - | Portland Timbers 2 | 5:2 | |
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| 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 |  |
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| 4. Round | 02/09/2020 | Portland Timbers 2 | - | Sacramento Republic | 1:2 | ||||
| 4. Round | 06/09/2020 | Reno 1868 FC | - | Portland Timbers 2 | 7:1 | ||||
| 4. Round | 10/09/2020 | Portland Timbers 2 | - | Tacoma Defiance | 3:0 | |
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| 4. Round | 17/09/2020 | Real Monarchs SLC | - | Portland Timbers 2 | 1:2 | ||||
| 4. Round | 21/09/2020 | Portland Timbers 2 | - | Reno 1868 FC | 2:5 | |
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| 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 |
USA