| 3. Journée | 16.05.2019 | Houston Dynamo | - | Portland Timbers | 1:1 |  |
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| 4. Journée | 23.06.2019 | Portland Timbers | - | Houston Dynamo | 4:0 | ||||
| 4. Journée | 27.06.2019 | Impact de Montréal | - | Portland Timbers | 2:1 | ||||
| 5. Journée | 08.07.2019 | New York City FC | - | Portland Timbers | 0:1 | ||||
| 5. Journée | 14.07.2019 | Portland Timbers | - | Colorado Rapids | 2:2 | |
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| 5. Journée | 28.07.2019 | Portland Timbers | - | Los Angeles Galaxy | 4:0 | |
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| 6. Journée | 11.08.2019 | Portland Timbers | - | Vancouver Whitecaps | 3:1 | ||||
| 6. Journée | 19.08.2019 | Portland Timbers | - | Atlanta United FC | 0:2 | ||||
| 7. Journée | 01.09.2019 | Portland Timbers | - | Real Salt Lake | 1:0 |  |
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| 7. Journée | 30.09.2019 | Sporting Kansas City | - | Portland Timbers | 2:2 | |
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