| 5. Round | 25/06/2023 | Portland Timbers | - | New York City FC | 1:1 | ||||
| 6. Round | 02/07/2023 | Minnesota United FC | - | Portland Timbers | 4:1 | ||||
| 6. Round | 13/07/2023 | Colorado Rapids | - | Portland Timbers | 0:0 | ||||
| 6. Round | 16/07/2023 | Portland Timbers | - | Columbus Crew | 3:2 | ||||
| 7. Round | 21/08/2023 | Houston Dynamo | - | Portland Timbers | 5:0 | ||||
| 7. Round | 27/08/2023 | Portland Timbers | - | Vancouver Whitecaps | 2:3 |  |
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| 7. Round | 31/08/2023 | Portland Timbers | - | Real Salt Lake | 2:1 | |
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| 8. Round | 03/09/2023 | Seattle Sounders | - | Portland Timbers | 2:2 | ||||
| 8. Round | 10/09/2023 | Portland Timbers | - | Los Angeles FC | 2:0 | ||||
| 8. Round | 18/09/2023 | Austin FC | - | Portland Timbers | 1:2 | |
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| 8. Round | 21/09/2023 | Portland Timbers | - | San Jose Earthquakes | 2:1 | ||||
| 8. Round | 24/09/2023 | Portland Timbers | - | Colorado Rapids | 3:2 | |
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| 8. Round | 01/10/2023 | Los Angeles Galaxy | - | Portland Timbers | 3:3 | |
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| 9. Round | 08/10/2023 | CF Montréal | - | Portland Timbers | 4:1 | ||||
| 9. Round | 22/10/2023 | Portland Timbers | - | Houston Dynamo | 1:3 | |
Chile