1. Round | 02/03/2019 | Colorado Rapids | - | Portland Timbers | 3:3 | ||||
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 | ||||
2. Round | 27/04/2019 | Toronto FC | - | Portland Timbers | 1:2 | ||||
3. Round | 05/05/2019 | Real Salt Lake | - | Portland Timbers | 1:2 | ||||
3. Round | 11/05/2019 | Vancouver Whitecaps | - | Portland Timbers | 1:0 | ||||
3. Round | 16/05/2019 | Houston Dynamo | - | Portland Timbers | 1:1 | ||||
3. Round | 26/05/2019 | Philadelphia Union | - | Portland Timbers | 1:3 | ||||
4. Round | 01/07/2019 | Portland Timbers | - | FC Dallas | 1:0 | ||||
5. Round | 07/07/2019 | New York City FC | - | Portland Timbers | 0:1 | ||||
5. Round | 28/07/2019 | Portland Timbers | - | Los Angeles Galaxy | 4:0 | ||||
7. Round | 01/09/2019 | Portland Timbers | - | Real Salt Lake | 1:0 | ||||
7. Round | 15/09/2019 | Portland Timbers | - | D.C. United | 0:1 | ||||
7. Round | 22/09/2019 | Portland Timbers | - | Minnesota United FC | 0:0 |