1. Round | 25/02/2024 | Portland Timbers | - | Colorado Rapids | 4:1 | ||||
2. Round | 03/03/2024 | Portland Timbers | - | D.C. United | 2:2 | ||||
2. Round | 09/03/2024 | New York City FC | - | Portland Timbers | 1:2 | ||||
2. Round | 17/03/2024 | Houston Dynamo | - | Portland Timbers | 1:0 | ||||
2. Round | 24/03/2024 | Portland Timbers | - | Philadelphia Union | 1:3 | ||||
2. Round | 31/03/2024 | Vancouver Whitecaps | - | Portland Timbers | 3:2 | ||||
4. Round | 05/05/2024 | Charlotte FC | - | Portland Timbers | 2:0 |