| Octavos de final | 27.10.2019 | Louisville City FC | - | Tampa Bay Rowdies | 2:1 | ||||
| Cuartos de final | 03.11.2019 | Pittsburgh Riverhounds | - | Louisville City FC | 1:2 pró. | ||||
| Semifinales | 09.11.2019 | Indy Eleven | - | Louisville City FC | 1:3 pró. |  |
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| Final | 18.11.2019 | Louisville City FC | - | Real Monarchs SLC | 1:3 |
Francia