1. Round | 10/03/2019 | Los Angeles FC | - | Portland Timbers | 4:1 | ||||
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 | 23/06/2019 | Portland Timbers | - | Houston Dynamo | 4:0 | ||||
4. Round | 27/06/2019 | Impact de Montréal | - | Portland Timbers | 2:1 | ||||
6. Round | 04/08/2019 | Minnesota United FC | - | Portland Timbers | 1:0 | ||||
6. Round | 11/08/2019 | Portland Timbers | - | Vancouver Whitecaps | 3:1 | ||||
6. Round | 15/08/2019 | Portland Timbers | - | Chicago Fire | 3:2 | ||||
6. Round | 19/08/2019 | Portland Timbers | - | Atlanta United FC | 0:2 | ||||
6. Round | 24/08/2019 | Portland Timbers | - | Seattle Sounders | 1:2 | ||||
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 |