| 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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| 8. Round | 25/02/2020 | NorthEast United FC | - | Chennaiyin FC | 2:2 |
India