| 3. Jornada | 26.05.2019 | Philadelphia Union | - | Portland Timbers | 1:3 | ||||
| 4. Jornada | 23.06.2019 | Portland Timbers | - | Houston Dynamo | 4:0 | ||||
| 4. Jornada | 27.06.2019 | Impact de Montréal | - | Portland Timbers | 2:1 | ||||
| 7. Jornada | 01.09.2019 | Portland Timbers | - | Real Salt Lake | 1:0 | ||||
| 7. Jornada | 08.09.2019 | Portland Timbers | - | Sporting Kansas City | 2:1 | ||||
| 7. Jornada | 15.09.2019 | Portland Timbers | - | D.C. United | 0:1 |  |
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| 7. Jornada | 26.09.2019 | Portland Timbers | - | New England Revolution | 2:2 |
Estados Unidos