| 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 | ||||
| 2. Round | 01/04/2019 | Los Angeles Galaxy | - | Portland Timbers | 2:1 | ||||
| 2. Round | 07/04/2019 | San Jose Earthquakes | - | Portland Timbers | 3:0 | ||||
| 2. Round | 14/04/2019 | FC Dallas | - | Portland Timbers | 2:1 | ||||
| 2. Round | 21/04/2019 | Columbus Crew | - | Portland Timbers | 1:3 | ||||
| 3. Round | 16/05/2019 | Houston Dynamo | - | Portland Timbers | 1:1 | ||||
| 4. Round | 02/06/2019 | Portland Timbers | - | Los Angeles FC | 2:3 | ||||
| 4. Round | 27/06/2019 | Impact de Montréal | - | Portland Timbers | 2:1 |
USA