| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 3/19/25 | Dempo vs Churchill Brothers | I-League | 1:3 | Yes | Yes |
| 12/18/24 | Churchill Brothers vs Dempo | I-League | 2:0 | No | No |
| 11/16/24 | Churchill Brothers vs Dempo | Club Friendly | 4:1 | Yes | Yes |
| 3/28/14 | Churchill Brothers vs Dempo | I-League | 1:4 | Yes | Yes |
| 11/6/13 | Dempo vs Churchill Brothers | I-League | 1:0 | No | No |
| 4/17/13 | Churchill Brothers vs Dempo | I-League | 2:2 | Yes | Yes |
| 10/6/12 | Dempo vs Churchill Brothers | I-League | 2:1 | Yes | Yes |
| 4/11/12 | Churchill Brothers vs Dempo | I-League | 2:4 | Yes | Yes |
| 12/4/11 | Dempo vs Churchill Brothers | I-League | 1:2 | Yes | Yes |
| 2/12/11 | Dempo vs Churchill Brothers | I-League | 2:0 | No | No |
| 12/4/10 | Churchill Brothers vs Dempo | I-League | 1:1 | No | Yes |
| 3/20/10 | Dempo vs Churchill Brothers | I-League | 4:2 | Yes | Yes |
| 11/8/09 | Churchill Brothers vs Dempo | I-League | 3:2 | Yes | Yes |
| 2/1/09 | Dempo vs Churchill Brothers | I-League | 1:1 | No | Yes |
| 11/5/08 | Churchill Brothers vs Dempo | I-League | 3:3 | Yes | Yes |
| 1/10/08 | Dempo vs Churchill Brothers | I-League | 4:1 | Yes | Yes |
| 12/4/07 | Churchill Brothers vs Dempo | I-League | 0:2 | No | No |
| 4/19/07 | Dempo vs Churchill Brothers | I-League | 3:1 | Yes | Yes |
| 3/4/07 | Churchill Brothers vs Dempo | I-League | 0:2 | No | No |