4. Round | 13/06/2019 | Seattle Sounders | - | Portland Timbers | 1:2 | ||||
Round of 16 | 20/06/2019 | Portland Timbers | - | Los Angeles Galaxy | 4:0 | ||||
Quarter-finals | 11/07/2019 | Los Angeles FC | - | Portland Timbers | 0:1 | ||||
Semi-finals | 08/08/2019 | Minnesota United FC | - | Portland Timbers | 2:1 |