 |
 |
| I-League | 04.01.2019 | Chennai City FC | - | Gokulam Kerala | 3:2 | ??? |
| I-League | 14.01.2019 | Chennai City FC | - | East Bengal FC | 2:1 | ??? |
| I-League | 18.01.2019 | Chennai City FC | - | Aizawl FC | 4:3 | ??? |
| Super League | 02.02.2019 | Chennaiyin FC | - | FC Pune City | 1:2 | ??? |
| Super League | 09.02.2019 | Chennaiyin FC | - | Bengaluru FC | 2:1 | 6.939 |
| Super League | 23.02.2019 | Chennaiyin FC | - | Jamshedpur FC | 0:0 | ??? |
| I-League | 24.02.2019 | Chennai City FC | - | Mohun Bagan FC | 3:1 | ??? |
| I-League | 28.02.2019 | Real Kashmir | - | East Bengal FC | 1:2 | ??? |
| I-League | 09.03.2019 | Chennai City FC | - | Minerva Punjab FC | 3:1 | ??? |
| Super League | 27.10.2019 | Chennaiyin FC | - | Mumbai City FC | 0:0 | 8.000 |
| Super League | 30.10.2019 | Chennaiyin FC | - | ATK | 0:1 | 8.000 |
| Super League | 25.11.2019 | Chennaiyin FC | - | Hyderabad FC | 2:1 | 7.500 |
| Super League | 28.11.2019 | Chennaiyin FC | - | Odisha FC | 2:2 | 8.693 |
| Super League | 20.12.2019 | Chennaiyin FC | - | Kerala Blasters | 3:1 | 11.597 |
| Super League | 26.12.2019 | Chennaiyin FC | - | FC Goa | 3:4 | 9.531 |
Indien