1. Round | 23/03/2019 | Philadelphia Union | - | Columbus Crew | 3:0 | ||||
3. Round | 02/05/2019 | Philadelphia Union | - | FC Cincinnati | 2:0 | ||||
3. Round | 05/05/2019 | Philadelphia Union | - | New England Revolution | 6:1 | ||||
3. Round | 11/05/2019 | Toronto FC | - | Philadelphia Union | 1:2 |