| 1. Round | 04/12/2019 | East Bengal FC | - | Real Kashmir | 1:1 | ||||
| 5. Round | 22/12/2019 | TRAU FC | - | Real Kashmir | 2:2 | ||||
| 2. Round | 26/12/2019 | Real Kashmir | - | Chennai City FC | 2:1 | ||||
| 6. Round | 05/01/2020 | Real Kashmir | - | Mohun Bagan FC | 0:2 | ||||
| 7. Round | 10/01/2020 | Real Kashmir | - | Punjab FC | 1:1 | ||||
| 8. Round | 14/01/2020 | NEROCA FC | - | Real Kashmir | 1:0 | ||||
| 10. Round | 26/01/2020 | Indian Arrows | - | Real Kashmir | 0:2 | ||||
| 11. Round | 01/02/2020 | Aizawl FC | - | Real Kashmir | 0:2 |  |
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| 12. Round | 08/02/2020 | Gokulam Kerala | - | Real Kashmir | 0:1 | ||||
| 14. Round | 16/02/2020 | Punjab FC | - | Real Kashmir | 1:0 | ||||
| 13. Round | 19/02/2020 | Churchill Brothers | - | Real Kashmir | 2:1 | ||||
| 15. Round | 24/02/2020 | Real Kashmir | - | Indian Arrows | 1:0 | ||||
| 16. Round | 29/02/2020 | Real Kashmir | - | Aizawl FC | 2:2 | |
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| 17. Round | 04/03/2020 | Real Kashmir | - | NEROCA FC | 1:0 | ||||
| 18. Round | 09/03/2020 | Real Kashmir | - | East Bengal FC | 0:1 |  |
England