3. Round | 16/05/2019 | Houston Dynamo | - | Portland Timbers | 1:1 | ||||
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 | ||||
5. Round | 14/07/2019 | Portland Timbers | - | Colorado Rapids | 2:2 | ||||
5. Round | 28/07/2019 | Portland Timbers | - | Los Angeles Galaxy | 4:0 | ||||
6. Round | 11/08/2019 | Portland Timbers | - | Vancouver Whitecaps | 3:1 | ||||
6. Round | 19/08/2019 | Portland Timbers | - | Atlanta United FC | 0:2 | ||||
7. Round | 01/09/2019 | Portland Timbers | - | Real Salt Lake | 1:0 | ||||
7. Round | 30/09/2019 | Sporting Kansas City | - | Portland Timbers | 2:2 |