11. Round | 29/12/2018 | Chennai City FC | - | Shillong Lajong FC | 6:1 | ||||
12. Round | 04/01/2019 | Chennai City FC | - | Gokulam Kerala | 3:2 | ||||
13. Round | 14/01/2019 | Chennai City FC | - | East Bengal FC | 2:1 | ||||
20. Round | 24/02/2019 | Chennai City FC | - | Mohun Bagan FC | 3:1 | ||||
21. Round | 01/03/2019 | Churchill Brothers | - | Chennai City FC | 3:2 | ||||
22. Round | 09/03/2019 | Chennai City FC | - | Minerva Punjab FC | 3:1 |