| 6. Round | 24/11/2018 | Chennai City FC | - | NEROCA FC | 2:1 | ||||
| 10. Round | 22/12/2018 | Chennai City FC | - | Real Kashmir | 0:1 | ||||
| 11. Round | 29/12/2018 | Chennai City FC | - | Shillong Lajong FC | 6:1 | ||||
| 17. Round | 08/02/2019 | Indian Arrows | - | Chennai City FC | 0:2 |  |
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| 22. Round | 09/03/2019 | Chennai City FC | - | Minerva Punjab FC | 3:1 |
India