2. Round | 16/04/2019 | Swope Park Rangers | - | Indy Eleven | 1:3 | ||||
2. Round | 28/04/2019 | New York RB II | - | Indy Eleven | 2:1 | ||||
3. Round | 26/05/2019 | Indy Eleven | - | Nashville SC | 0:0 | ||||
4. Round | 02/06/2019 | Indy Eleven | - | Pittsburgh Riverhounds | 2:1 | ||||
4. Round | 09/06/2019 | Memphis 901 | - | Indy Eleven | 0:3 | ||||
4. Round | 16/06/2019 | Loudoun United | - | Indy Eleven | 1:2 | ||||
4. Round | 23/06/2019 | Indy Eleven | - | Atlanta United II | 1:0 |