| 7. Jornada | 01.12.2018 | Mohun Bagan FC | - | Chennai City FC | 1:1 | ||||
| 9. Jornada | 16.12.2018 | Minerva Punjab FC | - | Chennai City FC | 0:0 | ||||
| 10. Jornada | 22.12.2018 | Chennai City FC | - | Real Kashmir | 0:1 |  |
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| 11. Jornada | 29.12.2018 | Chennai City FC | - | Shillong Lajong FC | 6:1 | ||||
| 12. Jornada | 04.01.2019 | Chennai City FC | - | Gokulam Kerala | 3:2 | ||||
| 13. Jornada | 14.01.2019 | Chennai City FC | - | East Bengal FC | 2:1 | ||||
| 14. Jornada | 18.01.2019 | Chennai City FC | - | Aizawl FC | 4:3 | ||||
| 15. Jornada | 28.01.2019 | Real Kashmir | - | Chennai City FC | 1:0 | ||||
| 17. Jornada | 08.02.2019 | Indian Arrows | - | Chennai City FC | 0:2 | ||||
| 18. Jornada | 11.02.2019 | NEROCA FC | - | Chennai City FC | 3:3 |
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