3. Round | 26/05/2019 | Philadelphia Union | - | Portland Timbers | 1:3 | ||||
4. Round | 23/06/2019 | Portland Timbers | - | Houston Dynamo | 4:0 | ||||
4. Round | 27/06/2019 | Impact de Montréal | - | Portland Timbers | 2:1 | ||||
7. Round | 01/09/2019 | Portland Timbers | - | Real Salt Lake | 1:0 | ||||
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 | 26/09/2019 | Portland Timbers | - | New England Revolution | 2:2 |