[10] Chennaiyin FC 2-1 Hyderabad FC [9] 2019-09-01 14:00
Stadium: Jawaharlal Nehru Stadium Round: 1
Referee: Lairenlakpam Ajit Metei Home Manager: John Gregory Away Manager: Philip Brown
Home History
| India Durand Cup | 2019/08/16 09:30 | Chennaiyin FC v Trau FC | W | 1-0 |
| AFC Champions League Two | 2019/06/26 10:30 | Manang Marshyangdi Club v Chennaiyin FC | W | 2-3 |
| AFC Champions League Two | 2019/06/19 09:30 | Punjab FC v Chennaiyin FC | D | 1-1 |
| AFC Champions League Two | 2019/05/15 13:00 | Dhaka Abahani v Chennaiyin FC | L | 3-2 |
| AFC Champions League Two | 2019/04/30 14:00 | Chennaiyin FC v Dhaka Abahani | W | 1-0 |
| AFC Champions League Two | 2019/04/17 14:00 | Chennaiyin FC v Manang Marshyangdi Club | W | 2-0 |
| India Super Cup | 2019/04/13 15:00 | FC Goa v Chennaiyin FC | L | 2-1 |
| India Super Cup | 2019/04/10 15:00 | ATK v Chennaiyin FC | W | 0-2 |
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