1. Round | 23/03/2019 | Philadelphia Union | - | Columbus Crew | 3:0 | ||||
5. Round | 04/07/2019 | Orlando City | - | Philadelphia Union | 1:3 | ||||
5. Round | 07/07/2019 | Philadelphia Union | - | Orlando City | 2:2 | ||||
5. Round | 14/07/2019 | Real Salt Lake | - | Philadelphia Union | 4:0 | ||||
5. Round | 21/07/2019 | Philadelphia Union | - | Chicago Fire | 2:0 | ||||
5. Round | 28/07/2019 | Impact de Montréal | - | Philadelphia Union | 4:0 | ||||
7. Round | 01/09/2019 | Philadelphia Union | - | Atlanta United FC | 3:1 | ||||
8. Round | 06/10/2019 | Philadelphia Union | - | New York City FC | 1:2 |