1. Round | 06/03/2016 | Portland Timbers | - | Columbus Crew | 2:1 | ||||
1. Round | 13/03/2016 | San Jose Earthquakes | - | Portland Timbers | 2:1 | ||||
1. Round | 20/03/2016 | Portland Timbers | - | Real Salt Lake | 2:2 | ||||
2. Round | 04/04/2016 | Orlando City | - | Portland Timbers | 4:1 | ||||
2. Round | 28/04/2016 | New England Revolution | - | Portland Timbers | 1:1 | ||||
3. Round | 01/05/2016 | Portland Timbers | - | Toronto FC | 2:1 | ||||
3. Round | 22/05/2016 | Portland Timbers | - | Vancouver Whitecaps | 4:2 | ||||
3. Round | 29/05/2016 | Chicago Fire | - | Portland Timbers | 1:1 | ||||
4. Round | 02/06/2016 | Portland Timbers | - | San Jose Earthquakes | 1:0 |