1. Round | 30/09/2018 | Bengaluru FC | - | Chennaiyin FC | 1:0 | ||||
2. Round | 06/10/2018 | Chennaiyin FC | - | FC Goa | 1:3 | ||||
2. Round | 18/10/2018 | Chennaiyin FC | - | NorthEast United FC | 3:4 | ||||
3. Round | 06/11/2018 | FC Pune City | - | Chennaiyin FC | 2:4 | ||||
3. Round | 25/11/2018 | Jamshedpur FC | - | Chennaiyin FC | 3:1 | ||||
3. Round | 29/11/2018 | Chennaiyin FC | - | Kerala Blasters | 0:0 | ||||
4. Round | 02/12/2018 | Chennaiyin FC | - | ATK | 2:3 | ||||
4. Round | 06/12/2018 | Mumbai City FC | - | Chennaiyin FC | 2:0 | ||||
4. Round | 15/12/2018 | Chennaiyin FC | - | Delhi Dynamos FC | 1:3 | ||||
6. Round | 15/02/2019 | Kerala Blasters | - | Chennaiyin FC | 3:0 | ||||
6. Round | 23/02/2019 | Chennaiyin FC | - | Jamshedpur FC | 0:0 | ||||
6. Round | 28/02/2019 | FC Goa | - | Chennaiyin FC | 1:0 |