| 5. Jornada | 25.06.2023 | Portland Timbers | - | New York City FC | 1:1 | ||||
| 6. Jornada | 02.07.2023 | Minnesota United FC | - | Portland Timbers | 4:1 | ||||
| 6. Jornada | 13.07.2023 | Colorado Rapids | - | Portland Timbers | 0:0 | ||||
| 6. Jornada | 16.07.2023 | Portland Timbers | - | Columbus Crew | 3:2 | ||||
| 7. Jornada | 21.08.2023 | Houston Dynamo | - | Portland Timbers | 5:0 | ||||
| 7. Jornada | 27.08.2023 | Portland Timbers | - | Vancouver Whitecaps | 2:3 |  |
|||
| 7. Jornada | 31.08.2023 | Portland Timbers | - | Real Salt Lake | 2:1 | |
|||
| 8. Jornada | 03.09.2023 | Seattle Sounders | - | Portland Timbers | 2:2 | ||||
| 8. Jornada | 10.09.2023 | Portland Timbers | - | Los Angeles FC | 2:0 | ||||
| 8. Jornada | 18.09.2023 | Austin FC | - | Portland Timbers | 1:2 | |
|||
| 8. Jornada | 21.09.2023 | Portland Timbers | - | San Jose Earthquakes | 2:1 | ||||
| 8. Jornada | 24.09.2023 | Portland Timbers | - | Colorado Rapids | 3:2 | |
 |
||
| 8. Jornada | 01.10.2023 | Los Angeles Galaxy | - | Portland Timbers | 3:3 | |
|||
| 9. Jornada | 08.10.2023 | CF Montréal | - | Portland Timbers | 4:1 | ||||
| 9. Jornada | 22.10.2023 | Portland Timbers | - | Houston Dynamo | 1:3 | |
Chile
