| 1. Round | 01/12/2019 | Chennai City FC | - | TRAU FC | 1:0 | ||||
| 3. Round | 10/12/2019 | Punjab FC | - | Chennai City FC | 3:1 | ||||
| 4. Round | 17/12/2019 | Aizawl FC | - | Chennai City FC | 1:1 | ||||
| 5. Round | 21/12/2019 | Chennai City FC | - | NEROCA FC | 2:2 | ||||
| 2. Round | 26/12/2019 | Real Kashmir | - | Chennai City FC | 2:1 | ||||
| 7. Round | 09/01/2020 | Gokulam Kerala | - | Chennai City FC | 2:3 |  |
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| 10. Round | 25/01/2020 | Chennai City FC | - | East Bengal FC | 0:2 | ||||
| 11. Round | 31/01/2020 | Chennai City FC | - | Mohun Bagan FC | 2:3 | |
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| 9. Round | 05/02/2020 | Chennai City FC | - | Indian Arrows | 1:0 | ||||
| 12. Round | 09/02/2020 | Churchill Brothers | - | Chennai City FC | 1:2 | ||||
| 13. Round | 12/02/2020 | Chennai City FC | - | Gokulam Kerala | 0:1 | ||||
| 14. Round | 16/02/2020 | TRAU FC | - | Chennai City FC | 0:0 | ||||
| 15. Round | 23/02/2020 | Chennai City FC | - | Aizawl FC | 1:1 | ||||
| 16. Round | 28/02/2020 | Indian Arrows | - | Chennai City FC | 0:2 | ||||
| 17. Round | 05/03/2020 | Mohun Bagan FC | - | Chennai City FC | 1:1 | ||||
| 19. Round | 14/03/2020 | NEROCA FC | - | Chennai City FC | 2:2 |  |
Spain