Stadium: TRC Turf Ground Round: 4
| India I-League | 2019/01/31 11:30 | Churchill Brothers SC v Real Kashmir FC | D | 1-1 |
| India I-League | 2018/11/06 08:30 | Real Kashmir FC v Churchill Brothers SC | D | 0-0 |
| India Super Cup | 2019/04/01 15:00 | ATK v Real Kashmir FC | L | 3-1 |
| India I-League | 2019/03/09 08:30 | Neroca FC v Real Kashmir FC | W | 2-3 |
| India I-League | 2019/02/28 08:30 | Real Kashmir FC v East Bengal Club | L | 1-2 |
| India I-League | 2019/02/24 08:30 | Indian Arrows v Real Kashmir FC | D | 2-2 |
| India I-League | 2019/02/06 08:30 | Real Kashmir FC v Gokulam Kerala FC | W | 1-0 |
| India I-League | 2019/01/31 11:30 | Churchill Brothers SC v Real Kashmir FC | D | 1-1 |
| India I-League | 2019/01/28 08:30 | Real Kashmir FC v Chennai City FC | W | 1-0 |
| India I-League | 2019/01/19 11:30 | Shillong Lajong FC v Real Kashmir FC | W | 0-1 |
| Other Match | 2019/03/21 10:20 | Churchill Brothers SC v FC Bardez | W | 3-0 |
| India I-League | 2019/03/09 08:30 | Aizawl FC v Churchill Brothers SC | L | 2-1 |
| India I-League | 2019/03/01 11:30 | Churchill Brothers SC v Chennai City FC | W | 3-2 |
| India I-League | 2019/02/17 11:30 | East Bengal Club v Churchill Brothers SC | D | 1-1 |
| India I-League | 2019/02/09 11:30 | Churchill Brothers SC v Mohun Bagan | D | 1-1 |
| India I-League | 2019/02/05 11:30 | Shillong Lajong FC v Churchill Brothers SC | L | 3-2 |
| India I-League | 2019/01/31 11:30 | Churchill Brothers SC v Real Kashmir FC | D | 1-1 |
| India Goa Pro League | 2019/01/28 10:30 | Churchill Brothers SC v Panjim Footballers | W | 1-0 |