| 1. Round | 17/03/2019 | FC Cincinnati | - | Portland Timbers | 3:0 | ||||
| 2. Round | 01/04/2019 | Los Angeles Galaxy | - | Portland Timbers | 2:1 | ||||
| 4. Round | 23/06/2019 | Portland Timbers | - | Houston Dynamo | 4:0 | ||||
| 4. Round | 27/06/2019 | Impact de Montréal | - | Portland Timbers | 2:1 | ||||
| 5. Round | 07/07/2019 | New York City FC | - | Portland Timbers | 0:1 |  |
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| 5. Round | 14/07/2019 | Portland Timbers | - | Colorado Rapids | 2:2 | ||||
| 5. Round | 19/07/2019 | Portland Timbers | - | Orlando City | 1:1 | |
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| 7. Round | 01/09/2019 | Portland Timbers | - | Real Salt Lake | 1:0 | |
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| 7. Round | 08/09/2019 | Portland Timbers | - | Sporting Kansas City | 2:1 | ||||
| 7. Round | 15/09/2019 | Portland Timbers | - | D.C. United | 0:1 | ||||
| 7. Round | 19/09/2019 | Portland Timbers | - | New York RB | 0:2 | ||||
| 7. Round | 22/09/2019 | Portland Timbers | - | Minnesota United FC | 0:0 | ||||
| 7. Round | 26/09/2019 | Portland Timbers | - | New England Revolution | 2:2 | ||||
| 7. Round | 30/09/2019 | Sporting Kansas City | - | Portland Timbers | 2:2 | ||||
| 8. Round | 06/10/2019 | Portland Timbers | - | San Jose Earthquakes | 3:1 |
France
Guadeloupe