| 1. Jornada | 17.03.2019 | FC Cincinnati | - | Portland Timbers | 3:0 | ||||
| 2. Jornada | 01.04.2019 | Los Angeles Galaxy | - | Portland Timbers | 2:1 | ||||
| 4. Jornada | 23.06.2019 | Portland Timbers | - | Houston Dynamo | 4:0 | ||||
| 4. Jornada | 27.06.2019 | Impact de Montréal | - | Portland Timbers | 2:1 | ||||
| 5. Jornada | 08.07.2019 | New York City FC | - | Portland Timbers | 0:1 |  |
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| 5. Jornada | 14.07.2019 | Portland Timbers | - | Colorado Rapids | 2:2 | ||||
| 5. Jornada | 19.07.2019 | Portland Timbers | - | Orlando City | 1:1 | |
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| 7. Jornada | 01.09.2019 | Portland Timbers | - | Real Salt Lake | 1:0 | |
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| 7. Jornada | 08.09.2019 | Portland Timbers | - | Sporting Kansas City | 2:1 | ||||
| 7. Jornada | 15.09.2019 | Portland Timbers | - | D.C. United | 0:1 | ||||
| 7. Jornada | 19.09.2019 | Portland Timbers | - | New York RB | 0:2 | ||||
| 7. Jornada | 22.09.2019 | Portland Timbers | - | Minnesota United FC | 0:0 | ||||
| 7. Jornada | 26.09.2019 | Portland Timbers | - | New England Revolution | 2:2 | ||||
| 7. Jornada | 30.09.2019 | Sporting Kansas City | - | Portland Timbers | 2:2 | ||||
| 8. Jornada | 06.10.2019 | Portland Timbers | - | San Jose Earthquakes | 3:1 |
Francia
Guadalupe