| Round of 16 | 26/10/2019 | Real Monarchs SLC | - | Orange County SC | 6:2 |  |
|||
| Quarter-finals | 02/11/2019 | Phoenix Rising | - | Real Monarchs SLC | 1:2 | |
|||
| Semi-finals | 09/11/2019 | Real Monarchs SLC | - | El Paso Locomotive | 2:1 aet | ||||
| Final | 18/11/2019 | Louisville City FC | - | Real Monarchs SLC | 1:3 |
Cuba