1. Round | 01/12/2019 | Chennai City FC | - | TRAU FC | 1:0 | ||||
3. Round | 10/12/2019 | Punjab FC | - | Chennai City FC | 3:1 | ||||
2. Round | 26/12/2019 | Real Kashmir | - | Chennai City FC | 2:1 | ||||
7. Round | 09/01/2020 | Gokulam Kerala | - | Chennai City FC | 2:3 | ||||
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 | ||||
9. Round | 05/02/2020 | Chennai City FC | - | Indian Arrows | 1:0 |