| 1. Jornada | 09.01.2021 | Gokulam Kerala | - | Chennai City FC | 1:2 |  |
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| 2. Jornada | 15.01.2021 | Chennai City FC | - | Real Kashmir | 0:2 | ||||
| 4. Jornada | 24.01.2021 | TRAU FC | - | Chennai City FC | 2:0 | ||||
| 6. Jornada | 03.02.2021 | Chennai City FC | - | Sudeva Delhi | 0:4 | ||||
| 7. Jornada | 09.02.2021 | NEROCA FC | - | Chennai City FC | 1:2 | ||||
| 8. Jornada | 13.02.2021 | Punjab FC | - | Chennai City FC | 2:0 | ||||
| 9. Jornada | 18.02.2021 | Chennai City FC | - | Churchill Brothers | 1:2 | |
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| 10. Jornada | 23.02.2021 | Mohammedan SC | - | Chennai City FC | 2:1 | ||||
| 11. Jornada | 28.02.2021 | Chennai City FC | - | Aizawl FC | 0:3 | |
India