| 1. Ronde | 01.12.2019 | Chennai City FC | - | TRAU FC | 1:0 | ||||
| 3. Ronde | 10.12.2019 | Punjab FC | - | Chennai City FC | 3:1 | ||||
| 2. Ronde | 26.12.2019 | Real Kashmir | - | Chennai City FC | 2:1 | ||||
| 7. Ronde | 09.01.2020 | Gokulam Kerala | - | Chennai City FC | 2:3 | ||||
| 10. Ronde | 25.01.2020 | Chennai City FC | - | East Bengal FC | 0:2 | ||||
| 11. Ronde | 31.01.2020 | Chennai City FC | - | Mohun Bagan FC | 2:3 | ||||
| 9. Ronde | 05.02.2020 | Chennai City FC | - | Indian Arrows | 1:0 |
India