| 5. Round | 09/12/2020 | Mumbai City FC | - | Chennaiyin FC | 2:1 | ||||
| 6. Round | 13/12/2020 | NorthEast United FC | - | Chennaiyin FC | 0:0 | ||||
| 7. Round | 19/12/2020 | FC Goa | - | Chennaiyin FC | 1:2 | ||||
| 8. Round | 26/12/2020 | SC East Bengal | - | Chennaiyin FC | 2:2 | ||||
| 9. Round | 29/12/2020 | Chennaiyin FC | - | ATK Mohun Bagan FC | 0:0 | ||||
| 10. Round | 04/01/2021 | Chennaiyin FC | - | Hyderabad FC | 1:4 | ||||
| 14. Round | 21/01/2021 | ATK Mohun Bagan FC | - | Chennaiyin FC | 1:0 | ||||
| 16. Round | 31/01/2021 | Hyderabad FC | - | Chennaiyin FC | 2:0 | ||||
| 21. Round | 21/02/2021 | Kerala Blasters | - | Chennaiyin FC | 1:1 |
India