| 1. Jornada | 01.12.2019 | Chennai City FC | - | TRAU FC | 1:0 | ||||
| 3. Jornada | 10.12.2019 | Punjab FC | - | Chennai City FC | 3:1 | ||||
| 4. Jornada | 17.12.2019 | Aizawl FC | - | Chennai City FC | 1:1 | ||||
| 5. Jornada | 21.12.2019 | Chennai City FC | - | NEROCA FC | 2:2 | ||||
| 2. Jornada | 26.12.2019 | Real Kashmir | - | Chennai City FC | 2:1 | ||||
| 7. Jornada | 09.01.2020 | Gokulam Kerala | - | Chennai City FC | 2:3 |  |
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| 10. Jornada | 25.01.2020 | Chennai City FC | - | East Bengal FC | 0:2 | ||||
| 11. Jornada | 31.01.2020 | Chennai City FC | - | Mohun Bagan FC | 2:3 | |
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| 9. Jornada | 05.02.2020 | Chennai City FC | - | Indian Arrows | 1:0 | ||||
| 12. Jornada | 09.02.2020 | Churchill Brothers | - | Chennai City FC | 1:2 | ||||
| 13. Jornada | 12.02.2020 | Chennai City FC | - | Gokulam Kerala | 0:1 | ||||
| 14. Jornada | 16.02.2020 | TRAU FC | - | Chennai City FC | 0:0 | ||||
| 15. Jornada | 23.02.2020 | Chennai City FC | - | Aizawl FC | 1:1 | ||||
| 16. Jornada | 28.02.2020 | Indian Arrows | - | Chennai City FC | 0:2 | ||||
| 17. Jornada | 05.03.2020 | Mohun Bagan FC | - | Chennai City FC | 1:1 | ||||
| 19. Jornada | 14.03.2020 | NEROCA FC | - | Chennai City FC | 2:2 |  |
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