| 14. Round | 18/01/2019 | Chennai City FC | - | Aizawl FC | 4:3 | ||||
| 17. Round | 08/02/2019 | Indian Arrows | - | Chennai City FC | 0:2 | ||||
| 18. Round | 11/02/2019 | NEROCA FC | - | Chennai City FC | 3:3 | ||||
| 19. Round | 18/02/2019 | Shillong Lajong FC | - | Chennai City FC | 2:4 | ||||
| 21. Round | 01/03/2019 | Churchill Brothers | - | Chennai City FC | 3:2 |
India