1. Round | 28/10/2018 | Minerva Punjab FC | - | Churchill Brothers | 0:0 | ||||
2. Round | 01/11/2018 | Chennai City FC | - | Churchill Brothers | 2:2 | ||||
3. Round | 06/11/2018 | Real Kashmir | - | Churchill Brothers | 0:0 | ||||
6. Round | 25/11/2018 | Mohun Bagan FC | - | Churchill Brothers | 0:3 | ||||
7. Round | 30/11/2018 | Gokulam Kerala | - | Churchill Brothers | 1:1 | ||||
8. Round | 09/12/2018 | Churchill Brothers | - | Aizawl FC | 4:1 | ||||
9. Round | 15/12/2018 | NEROCA FC | - | Churchill Brothers | 2:1 | ||||
11. Round | 30/12/2018 | Indian Arrows | - | Churchill Brothers | 0:1 | ||||
12. Round | 05/01/2019 | Churchill Brothers | - | Minerva Punjab FC | 2:0 | ||||
13. Round | 10/01/2019 | Churchill Brothers | - | Gokulam Kerala | 3:1 | ||||
14. Round | 19/01/2019 | Churchill Brothers | - | NEROCA FC | 2:1 | ||||
15. Round | 26/01/2019 | Churchill Brothers | - | Indian Arrows | 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 |