1. Round | 28/10/2018 | Minerva Punjab FC | - | 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 | ||||
7. Round | 30/11/2018 | Gokulam Kerala | - | Churchill Brothers | 1:1 | ||||
11. Round | 30/12/2018 | Indian Arrows | - | Churchill Brothers | 0:1 | ||||
22. Round | 09/03/2019 | Aizawl FC | - | Churchill Brothers | 2:1 |