| 2. Jornada | 01.11.2018 | Chennai City FC | - | Churchill Brothers | 2:2 | ||||
| 3. Jornada | 04.11.2018 | Gokulam Kerala | - | Chennai City FC | 2:3 |  |
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| 4. Jornada | 13.11.2018 | East Bengal FC | - | Chennai City FC | 1:2 | ||||
| 6. Jornada | 24.11.2018 | Chennai City FC | - | NEROCA FC | 2:1 | ||||
| 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 | ||||
| 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 | ||||
| 19. Jornada | 18.02.2019 | Shillong Lajong FC | - | Chennai City FC | 2:4 |
India