| 1. Round | 23/10/2019 | FC Goa | - | Chennaiyin FC | 3:0 | ||||
| 2. Round | 27/10/2019 | Chennaiyin FC | - | Mumbai City FC | 0:0 | ||||
| 3. Round | 30/10/2019 | Chennaiyin FC | - | ATK | 0:1 | ||||
| 4. Round | 10/11/2019 | Bengaluru FC | - | Chennaiyin FC | 3:0 |  |
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| 5. Round | 25/11/2019 | Chennaiyin FC | - | Hyderabad FC | 2:1 | ||||
| 6. Round | 28/11/2019 | Chennaiyin FC | - | Odisha FC | 2:2 | ||||
| 7. Round | 09/12/2019 | Jamshedpur FC | - | Chennaiyin FC | 1:1 | ||||
| 9. Round | 20/12/2019 | Chennaiyin FC | - | Kerala Blasters | 3:1 | |
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| 10. Round | 26/12/2019 | Chennaiyin FC | - | FC Goa | 3:4 | ||||
| 11. Round | 06/01/2020 | Odisha FC | - | Chennaiyin FC | 2:0 | ||||
| 12. Round | 10/01/2020 | Hyderabad FC | - | Chennaiyin FC | 1:3 | ||||
| 13. Round | 16/01/2020 | Chennaiyin FC | - | NorthEast United FC | 2:0 | ||||
| 14. Round | 23/01/2020 | Chennaiyin FC | - | Jamshedpur FC | 4:1 | ||||
| 15. Round | 01/02/2020 | Kerala Blasters | - | Chennaiyin FC | 3:6 | ||||
| 16. Round | 09/02/2020 | Chennaiyin FC | - | Bengaluru FC | 0:0 | ||||
| 17. Round | 16/02/2020 | ATK | - | Chennaiyin FC | 1:3 | ||||
| 18. Round | 21/02/2020 | Mumbai City FC | - | Chennaiyin FC | 0:1 | |
India