| Round of 16 | 21/10/2018 | Louisville City FC | - | Indy Eleven | 4:1 | ||||
| Quarter-finals | 28/10/2018 | Louisville City FC | - | Bethlehem Steel FC | 2:0 | ||||
| Semi-finals | 02/11/2018 | Louisville City FC | - | New York RB II | 5:1 |  |
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| Final | 09/11/2018 | Louisville City FC | - | Phoenix Rising | 1:0 | |
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USA