2. Round | 02/05/2021 | Birmingham Legion | - | Indy Eleven | 0:1 | ||||
2. Round | 09/05/2021 | Indy Eleven | - | FC Tulsa | 0:2 | ||||
2. Round | 23/05/2021 | Indy Eleven | - | Sporting Kansas City 2 | 2:0 | ||||
2. Round | 30/05/2021 | Louisville City FC | - | Indy Eleven | 1:2 | ||||
3. Round | 03/06/2021 | Indy Eleven | - | OKC Energy FC | 1:1 | ||||
3. Round | 06/06/2021 | Indy Eleven | - | Memphis 901 | 1:2 | ||||
3. Round | 10/06/2021 | El Paso Locomotive | - | Indy Eleven | 2:0 | ||||
3. Round | 16/06/2021 | Indy Eleven | - | Pittsburgh Riverhounds | 0:1 | ||||
3. Round | 20/06/2021 | Sporting Kansas City 2 | - | Indy Eleven | 1:2 | ||||
3. Round | 27/06/2021 | Louisville City FC | - | Indy Eleven | 3:3 | ||||
4. Round | 04/07/2021 | Indy Eleven | - | Birmingham Legion | 0:1 | ||||
4. Round | 08/07/2021 | Atlanta United II | - | Indy Eleven | 1:1 | ||||
4. Round | 18/07/2021 | Indy Eleven | - | Memphis 901 | 1:1 | ||||
4. Round | 25/07/2021 | Indy Eleven | - | Birmingham Legion | 1:2 | ||||
5. Round | 05/08/2021 | FC Tulsa | - | Indy Eleven | 0:2 | ||||
5. Round | 09/08/2021 | Atlanta United II | - | Indy Eleven | 6:2 | ||||
5. Round | 19/08/2021 | Loudoun United | - | Indy Eleven | 4:1 | ||||
5. Round | 22/08/2021 | Sporting Kansas City 2 | - | Indy Eleven | 1:1 |