| 28/06/2026 03:00 | | Portland Timbers Reserve  | 2 - 3 | San Jose Earthquakes Reserve | B |
| 21/06/2026 07:00 | | Colorado Rapids II | 0 - 2 | Portland Timbers Reserve | T |
| 14/06/2026 04:30 | | Real Monarchs | 4 - 1 | Portland Timbers Reserve | B |
| 06/06/2026 08:00 | | Vancouver Whitecaps Reserve | 0 - 1 | Portland Timbers Reserve | T |
| 01/06/2026 03:00 | | Portland Timbers Reserve | 1 - 0 | Tacoma Defiance | T |
| 25/05/2026 03:00 | | Portland Timbers Reserve | 0 - 3 | Houston Dynamo B | B |
| 18/05/2026 08:00 | | San Jose Earthquakes Reserve | 0 - 1 | Portland Timbers Reserve | T |
| 14/05/2026 07:00 | | Portland Timbers Reserve | 2 - 1 | MINNESOTA United B | T |
| 11/05/2026 03:00 | | Portland Timbers Reserve | 3 - 3 | Ventura County FC | H |
| 04/05/2026 04:30 | | Real Monarchs | 0 - 3 | Portland Timbers Reserve | T |
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