[1] Chennai City FC 2-1 East Bengal Club [6] 2019-01-14 11:30
Stadium: Jawaharlal Nehru Stadium Round: 1
Head to Head
| India I-League | 2018/11/13 11:30 | East Bengal Club v Chennai City FC | W | 1-2 |
| India I-League | 2018/02/24 08:30 | East Bengal Club v Chennai City FC | L | 7-1 |
| India I-League | 2017/12/22 12:00 | Chennai City FC v East Bengal Club | L | 1-2 |
| India Federation Cup | 2017/05/09 10:30 | Chennai City FC v East Bengal Club | L | 0-2 |
| India I-League | 2017/03/12 13:35 | Chennai City FC v East Bengal Club | W | 2-1 |
| India I-League | 2017/02/05 13:35 | East Bengal Club v Chennai City FC | L | 3-0 |
Home History
| India I-League | 2019/01/04 11:30 | Chennai City FC v Gokulam Kerala FC | W | 3-2 |
| India I-League | 2018/12/29 11:30 | Chennai City FC v Shillong Lajong FC | W | 6-1 |
| India I-League | 2018/12/22 14:00 | Chennai City FC v Real Kashmir FC | L | 0-1 |
| India I-League | 2018/12/16 08:30 | Punjab FC v Chennai City FC | D | 0-0 |
| India I-League | 2018/12/01 11:30 | Mohun Bagan v Chennai City FC | D | 1-1 |
| India I-League | 2018/11/24 11:30 | Chennai City FC v Neroca FC | W | 2-1 |
| India I-League | 2018/11/16 08:30 | Aizawl FC v Chennai City FC | W | 1-2 |
| India I-League | 2018/11/13 11:30 | East Bengal Club v Chennai City FC | W | 1-2 |
Away History
| India I-League | 2019/01/08 08:30 | Indian Arrows v East Bengal Club | W | 1-2 |
| India I-League | 2018/12/28 11:30 | East Bengal Club v Real Kashmir FC | D | 1-1 |
| India I-League | 2018/12/20 11:30 | Churchill Brothers SC v East Bengal Club | W | 1-2 |
| India I-League | 2018/12/16 11:30 | East Bengal Club v Mohun Bagan | W | 3-2 |
| India I-League | 2018/12/08 11:30 | East Bengal Club v Gokulam Kerala FC | W | 3-1 |
| India I-League | 2018/12/04 11:30 | East Bengal Club v Punjab FC | L | 0-1 |
| India I-League | 2018/11/24 08:30 | Aizawl FC v East Bengal Club | L | 3-2 |
| India I-League | 2018/11/13 11:30 | East Bengal Club v Chennai City FC | L | 1-2 |