3. Round | 06/11/2018 | Real Kashmir | - | Churchill Brothers | 0:0 | ||||
5. Round | 15/11/2018 | Churchill Brothers | - | Shillong Lajong FC | 4:2 | ||||
6. Round | 25/11/2018 | Mohun Bagan FC | - | Churchill Brothers | 0:3 | ||||
9. Round | 15/12/2018 | NEROCA FC | - | Churchill Brothers | 2:1 | ||||
16. Round | 31/01/2019 | Churchill Brothers | - | Real Kashmir | 1:1 | ||||
17. Round | 05/02/2019 | Shillong Lajong FC | - | Churchill Brothers | 3:2 | ||||
18. Round | 09/02/2019 | Churchill Brothers | - | Mohun Bagan FC | 1:1 | ||||
19. Round | 17/02/2019 | East Bengal FC | - | Churchill Brothers | 1:1 | ||||
21. Round | 01/03/2019 | Churchill Brothers | - | Chennai City FC | 3:2 | ||||
22. Round | 09/03/2019 | Aizawl FC | - | Churchill Brothers | 2:1 |