| Cuarta Ronda | 06.06.2018 | Philadelphia Union | - | Richmond Kickers | 5:0 | ||||
| Octavos de final | 17.06.2018 | Philadelphia Union | - | New York RB | 2:1 |  |
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| Cuartos de final | 19.07.2018 | Philadelphia Union | - | Orlando City | 1:0 | ||||
| Semifinales | 09.08.2018 | Philadelphia Union | - | Chicago Fire | 3:0 | |
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| Final | 27.09.2018 | Houston Dynamo | - | Philadelphia Union | 3:0 |
Jamaica