| Round of 16 | 27/10/2019 | Louisville City FC | - | Tampa Bay Rowdies | 2:1 | ||||
| Quarter-finals | 02/11/2019 | Pittsburgh Riverhounds | - | Louisville City FC | 1:2 aet | ||||
| Semi-finals | 09/11/2019 | Indy Eleven | - | Louisville City FC | 1:3 aet |  |
|||
| Final | 18/11/2019 | Louisville City FC | - | Real Monarchs SLC | 1:3 | |
| Devon Chesterton Williams | |
| Born: | 08.04.1992 |
| Place of birth: |
Kingston, 
Jamaica |
| Nationality: |
Jamaica
|
| Height: | 170 cm |
| Weight: | 68 kg |
| Position(s): | Offensive Midfielder Central Midfielder |
| Foot: | right |
