| 3. Jornada | 16.05.2019 | Houston Dynamo | - | Portland Timbers | 1:1 |  |
|||
| 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 | ||||
| 5. Jornada | 14.07.2019 | Portland Timbers | - | Colorado Rapids | 2:2 | |
|||
| 5. Jornada | 28.07.2019 | Portland Timbers | - | Los Angeles Galaxy | 4:0 | |
|||
| 6. Jornada | 11.08.2019 | Portland Timbers | - | Vancouver Whitecaps | 3:1 | ||||
| 6. Jornada | 19.08.2019 | Portland Timbers | - | Atlanta United FC | 0:2 | ||||
| 7. Jornada | 01.09.2019 | Portland Timbers | - | Real Salt Lake | 1:0 |  |
|||
| 7. Jornada | 30.09.2019 | Sporting Kansas City | - | Portland Timbers | 2:2 | |
Venezuela