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 |