| tour des 16 | 27.10.2019 | Louisville City FC | - | Tampa Bay Rowdies | 2:1 |  |
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| Quarts de finale | 03.11.2019 | Pittsburgh Riverhounds | - | Louisville City FC | 1:2 ap | ||||
| Demi-finales | 09.11.2019 | Indy Eleven | - | Louisville City FC | 1:3 ap | |
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| Finale | 18.11.2019 | Louisville City FC | - | Real Monarchs SLC | 1:3 | |
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