| 1. Round | 09/01/2021 | Gokulam Kerala | - | Chennai City FC | 1:2 | ||||
| 2. Round | 15/01/2021 | Chennai City FC | - | Real Kashmir | 0:2 | ||||
| 4. Round | 24/01/2021 | TRAU FC | - | Chennai City FC | 2:0 | ||||
| 5. Round | 29/01/2021 | Chennai City FC | - | Indian Arrows | 1:0 | ||||
| 6. Round | 03/02/2021 | Chennai City FC | - | Sudeva Delhi | 0:4 | ||||
| 7. Round | 09/02/2021 | NEROCA FC | - | Chennai City FC | 1:2 |  |
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| 8. Round | 13/02/2021 | Punjab FC | - | Chennai City FC | 2:0 | |
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| 9. Round | 18/02/2021 | Chennai City FC | - | Churchill Brothers | 1:2 | ||||
| 10. Round | 23/02/2021 | Mohammedan SC | - | Chennai City FC | 2:1 | ||||
| 11. Round | 28/02/2021 | Chennai City FC | - | Aizawl FC | 0:3 |
India