| 1. Round | 23/02/2025 | Portland Timbers | - | Vancouver Whitecaps | 1:4 | ||||
| 2. Round | 02/03/2025 | Portland Timbers | - | Austin FC | 1:0 | ||||
| 3. Round | 09/03/2025 | Nashville SC | - | Portland Timbers | 2:0 | ||||
| 4. Round | 16/03/2025 | Portland Timbers | - | Los Angeles Galaxy | 1:1 |  |
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| 5. Round | 23/03/2025 | Colorado Rapids | - | Portland Timbers | 0:3 | ||||
| 6. Round | 31/03/2025 | Portland Timbers | - | Houston Dynamo | 3:1 | |
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| 7. Round | 06/04/2025 | Austin FC | - | Portland Timbers | 0:0 | ||||
| 8. Round | 13/04/2025 | Sporting Kansas City | - | Portland Timbers | 2:4 | ||||
| 9. Round | 20/04/2025 | Portland Timbers | - | Los Angeles FC | 3:3 | |
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| 10. Round | 28/04/2025 | Los Angeles Galaxy | - | Portland Timbers | 2:4 | ||||
| 11. Round | 04/05/2025 | San Jose Earthquakes | - | Portland Timbers | 4:1 | |
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| 12. Round | 11/05/2025 | Portland Timbers | - | Sporting Kansas City | 1:0 | ||||
| 13. Round | 15/05/2025 | Real Salt Lake | - | Portland Timbers | 0:0 | ||||
| 14. Round | 18/05/2025 | Portland Timbers | - | Seattle Sounders | 1:1 | ||||
| 15. Round | 25/05/2025 | Orlando City | - | Portland Timbers | 1:0 |
Chile