| 1. Round | 02/03/2019 | Colorado Rapids | - | Portland Timbers | 3:3 | ||||
| 1. Round | 10/03/2019 | Los Angeles FC | - | Portland Timbers | 4:1 | ||||
| 1. Round | 17/03/2019 | FC Cincinnati | - | Portland Timbers | 3:0 |  |
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| 2. Round | 01/04/2019 | Los Angeles Galaxy | - | Portland Timbers | 2:1 | ||||
| 2. Round | 21/04/2019 | Columbus Crew | - | Portland Timbers | 1:3 | ||||
| 3. Round | 05/05/2019 | Real Salt Lake | - | Portland Timbers | 1:2 | ||||
| 3. Round | 11/05/2019 | Vancouver Whitecaps | - | Portland Timbers | 1:0 | ||||
| 4. Round | 27/06/2019 | Impact de Montréal | - | Portland Timbers | 2:1 |
Argentina
Italy