India: I-League - Losers stage |
| 5. Round | Neroca FC | Chennai City | 1:2 (0:1, 1:1) | details | 25.03.2021 |
| 4. Round | Chennai City | Aizawl | 1:3 (0:2, 1:1) | details | 20.03.2021 |
| 2. Round | Indian Arrows | Chennai City | 0:5 (0:1, 0:4) | details | 11.03.2021 |
| 1. Round | Chennai City | Sudeva Delhi | 1:2 (1:2, 0:0) | details | 06.03.2021 |
India: I-League - Main |
| 11. Round | Chennai City | Aizawl | 0:3 (0:2, 0:1) | details | 28.02.2021 |
| 10. Round | Mohammedan | Chennai City | 2:1 (0:1, 2:0) | details | 23.02.2021 |
| 9. Round | Chennai City | Churchill Brothers | 1:2 (0:0, 1:2) | details | 18.02.2021 |
| 8. Round | Punjab | Chennai City | 2:0 (1:0, 1:0) | details | 13.02.2021 |
| 7. Round | Neroca FC | Chennai City | 1:2 (0:1, 1:1) | details | 09.02.2021 |
| 6. Round | Chennai City | Sudeva Delhi | 0:4 (0:2, 0:2) | details | 03.02.2021 |
| 5. Round | Chennai City | Indian Arrows | 1:0 (0:0, 1:0) | details | 29.01.2021 |
| 4. Round | TRAU FC | Chennai City | 2:0 (0:0, 2:0) | details | 24.01.2021 |
| 2. Round | Chennai City | Real Kashmir | 0:2 (0:1, 0:1) | details | 15.01.2021 |
| 1. Round | Gokulam | Chennai City | 1:2 (1:1, 0:1) | details | 09.01.2021 |
Asia: AFC Cup - Main |
| Group E - 6. Round | Chennai City | TC Sports Club | CAN. | details | 04.11.2020 |
| Group E - 5. Round | Maziya | Chennai City | CAN. | details | 01.11.2020 |
| Group E - 4. Round | Bashundara Kings | Chennai City | CAN. | details | 29.10.2020 |
| Group E - 3. Round | Chennai City | Bashundara Kings | CAN. | details | 26.10.2020 |
| Group E - 2. Round | TC Sports Club | Chennai City | CAN. | details | 23.10.2020 |
India: I-League - Main |
| 22. Round | Chennai City | Real Kashmir | CAN. | details | 12.04.2020 |
| 21. Round | Chennai City | Punjab | CAN. | details | 05.04.2020 |
| 8. Round | Chennai City | Churchill Brothers | CAN. | details | 29.03.2020 |
| 20. Round | East Bengal | Chennai City | CAN. | details | 22.03.2020 |
| 19. Round | Neroca FC | Chennai City | 2:2 (1:2, 1:0) | details | 14.03.2020 |
Asia: AFC Cup - Main |
| Group E - 1. Round | Chennai City | Maziya | 2:2 (1:0, 1:2) | details | 11.03.2020 |
India: I-League - Main |
| 17. Round | Mohun Bagan | Chennai City | 1:1 (1:0, 0:1) | details | 05.03.2020 |
| 16. Round | Indian Arrows | Chennai City | 0:2 (0:0, 0:2) | details | 28.02.2020 |
| 15. Round | Chennai City | Aizawl | 1:1 (1:0, 0:1) | details | 23.02.2020 |
| 14. Round | TRAU FC | Chennai City | 0:0 (0:0, 0:0) | details | 16.02.2020 |
| 13. Round | Chennai City | Gokulam | 0:1 (0:0, 0:1) | details | 12.02.2020 |
| 12. Round | Churchill Brothers | Chennai City | 1:2 (0:0, 1:2) | details | 09.02.2020 |
| 9. Round | Chennai City | Indian Arrows | 1:0 (0:0, 1:0) | details | 05.02.2020 |
| 11. Round | Chennai City | Mohun Bagan | 2:3 (0:2, 2:1) | details | 31.01.2020 |
| 10. Round | Chennai City | East Bengal | 0:2 (0:0, 0:2) | details | 25.01.2020 |
Asia: AFC Champions League - Qualification |
| Quarter-finals | Chennai City | Al Riffa | 0:1 (0:1, 0:0) | details | 14.01.2020 |
India: I-League - Main |
| 7. Round | Gokulam | Chennai City | 2:3 (0:1, 2:2) | details | 09.01.2020 |
| 2. Round | Real Kashmir | Chennai City | 2:1 (2:0, 0:1) | details | 26.12.2019 |
| 5. Round | Chennai City | Neroca FC | 2:2 (2:1, 0:1) | details | 21.12.2019 |
| 4. Round | Aizawl | Chennai City | 1:1 (1:1, 0:0) | details | 17.12.2019 |
| 3. Round | Punjab | Chennai City | 3:1 (0:0, 3:1) | details | 10.12.2019 |
| 1. Round | Chennai City | TRAU FC | 1:0 (0:0, 1:0) | details | 01.12.2019 |
World: Club Friendly - Main |
| | Gokulam | Chennai City | 2:0 (2:0, 0:0) | details | 26.10.2019 |
| | Bashundara Kings | Chennai City | 3:2 (1:1, 2:1) | details | 24.10.2019 |
| | Chennai City | Terengganu | 3:5 (2:3, 1:2) | details | 22.10.2019 |
India: Durand Cup - Main |
| Group C | Chennai City | Army Green | 2:1 (1:1, 1:0) | details | 18.08.2019 |
| Group C | Chennai City | Goa | 1:2 (1:2, 0:0) | details | 14.08.2019 |
| Group C | Real Kashmir | Chennai City | 1:0 (0:0, 1:0) | details | 07.08.2019 |
India: Hero Super Cup - Main |
| Semi-finals | Chennai City | Goa | 0:3 (0:2, 0:1) | details | 09.04.2019 |
| Quarter-finals | Bengaluru FC | Chennai City | 1:2 (0:1, 1:1) | details | 04.04.2019 |
| 1/8-finals | Pune City | Chennai City | 2:4 (1:2, 1:2) | details | 31.03.2019 |