| 1. Jornada | 03.03.2019 | Colorado Rapids | - | Portland Timbers | 3:3 | ||||
| 1. Jornada | 11.03.2019 | Los Angeles FC | - | Portland Timbers | 4:1 | ||||
| 1. Jornada | 17.03.2019 | FC Cincinnati | - | Portland Timbers | 3:0 |  |
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| 2. Jornada | 01.04.2019 | Los Angeles Galaxy | - | Portland Timbers | 2:1 | ||||
| 2. Jornada | 21.04.2019 | Columbus Crew | - | Portland Timbers | 1:3 | ||||
| 3. Jornada | 05.05.2019 | Real Salt Lake | - | Portland Timbers | 1:2 | ||||
| 3. Jornada | 11.05.2019 | Vancouver Whitecaps | - | Portland Timbers | 1:0 | ||||
| 4. Jornada | 27.06.2019 | Impact de Montréal | - | Portland Timbers | 2:1 |
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