| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 5/18/25 | Kilmarnock vs Hearts | Premier League | 0:1 | No | No |
| 1/25/25 | Hearts vs Kilmarnock | Premier League | 3:2 | Yes | Yes |
| 12/15/24 | Kilmarnock vs Hearts | Premier League | 1:0 | No | No |
| 10/30/24 | Hearts vs Kilmarnock | Premier League | 1:2 | Yes | Yes |
| 4/27/24 | Kilmarnock vs Hearts | Premier League | 0:0 | No | No |
| 3/30/24 | Hearts vs Kilmarnock | Premier League | 1:1 | No | Yes |
| 12/2/23 | Kilmarnock vs Hearts | Premier League | 0:1 | No | No |
| 9/26/23 | Kilmarnock vs Hearts | Insurance League Cup | 1:2 | Yes | Yes |
| 8/13/23 | Hearts vs Kilmarnock | Premier League | 0:0 | No | No |
| 4/1/23 | Kilmarnock vs Hearts | Premier League | 2:1 | Yes | Yes |
| 12/17/22 | Hearts vs Kilmarnock | Premier League | 3:1 | Yes | Yes |
| 10/9/22 | Kilmarnock vs Hearts | Premier League | 2:2 | Yes | Yes |
| 8/31/22 | Hearts vs Kilmarnock | Insurance League Cup | 0:1 | No | No |
| 2/5/20 | Hearts vs Kilmarnock | Premier League | 2:3 | Yes | Yes |
| 11/23/19 | Kilmarnock vs Hearts | Premier League | 3:0 | Yes | No |
| 10/5/19 | Hearts vs Kilmarnock | Premier League | 0:1 | No | No |
| 5/4/19 | Hearts vs Kilmarnock | Premier League | 0:1 | No | No |
| 2/1/19 | Kilmarnock vs Hearts | Premier League | 1:2 | Yes | Yes |
| 11/10/18 | Hearts vs Kilmarnock | Premier League | 0:1 | No | No |
| 8/25/18 | Kilmarnock vs Hearts | Premier League | 0:1 | No | No |
| 2/27/18 | Hearts vs Kilmarnock | Premier League | 1:1 | No | Yes |
| 11/5/17 | Hearts vs Kilmarnock | Premier League | 1:2 | Yes | Yes |
| 8/12/17 | Kilmarnock vs Hearts | Premier League | 0:1 | No | No |
| 4/14/17 | Kilmarnock vs Hearts | Premier League | 0:0 | No | No |
| 12/27/16 | Hearts vs Kilmarnock | Premier League | 4:0 | Yes | No |
| 10/26/16 | Kilmarnock vs Hearts | Premier League | 2:0 | No | No |
| 2/27/16 | Hearts vs Kilmarnock | Premier League | 1:0 | No | No |
| 1/2/16 | Kilmarnock vs Hearts | Premier League | 2:2 | Yes | Yes |
| 10/3/15 | Hearts vs Kilmarnock | Premier League | 1:1 | No | Yes |
| 9/23/15 | Kilmarnock vs Hearts | Insurance League Cup | 2:3 | Yes | Yes |
| 5/4/14 | Hearts vs Kilmarnock | Premier League | 5:0 | Yes | No |
| 3/8/14 | Kilmarnock vs Hearts | Premier League | 4:2 | Yes | Yes |
| 12/26/13 | Hearts vs Kilmarnock | Premier League | 0:4 | Yes | No |
| 10/26/13 | Kilmarnock vs Hearts | Premier League | 2:0 | No | No |
| 4/20/13 | Kilmarnock vs Hearts | Premier League | 0:1 | No | No |
| 2/16/13 | Hearts vs Kilmarnock | Premier League | 0:3 | Yes | No |
| 12/26/12 | Kilmarnock vs Hearts | Premier League | 1:0 | No | No |
| 9/29/12 | Hearts vs Kilmarnock | Premier League | 1:3 | Yes | Yes |
| 2/11/12 | Kilmarnock vs Hearts | Premier League | 1:1 | No | Yes |
| 10/29/11 | Hearts vs Kilmarnock | Premier League | 0:1 | No | No |
| 8/21/11 | Kilmarnock vs Hearts | Premier League | 0:0 | No | No |
| 4/30/11 | Kilmarnock vs Hearts | Premier League | 2:2 | Yes | Yes |
| 3/5/11 | Hearts vs Kilmarnock | Premier League | 0:2 | No | No |
| 1/18/11 | Kilmarnock vs Hearts | Premier League | 1:2 | Yes | Yes |
| 10/31/10 | Hearts vs Kilmarnock | Premier League | 0:3 | Yes | No |
| 11/28/09 | Kilmarnock vs Hearts | Premier League | 1:2 | Yes | Yes |
| 9/15/09 | Hearts vs Kilmarnock | Premier League | 1:0 | No | No |
| 1/17/09 | Kilmarnock vs Hearts | Premier League | 0:2 | No | No |
| 10/4/08 | Hearts vs Kilmarnock | Premier League | 1:2 | Yes | Yes |
| 5/10/08 | Hearts vs Kilmarnock | Premier League | 0:2 | No | No |
| 1/5/08 | Hearts vs Kilmarnock | Premier League | 1:1 | No | Yes |
| 10/27/07 | Kilmarnock vs Hearts | Premier League | 3:1 | Yes | Yes |
| 5/20/07 | Kilmarnock vs Hearts | Premier League | 1:0 | No | No |
| 12/30/06 | Kilmarnock vs Hearts | Premier League | 0:0 | No | No |
| 10/21/06 | Hearts vs Kilmarnock | Premier League | 0:2 | No | No |
| 4/15/06 | Hearts vs Kilmarnock | Premier League | 2:0 | No | No |
| 1/21/06 | Kilmarnock vs Hearts | Premier League | 1:0 | No | No |
| 1/7/06 | Hearts vs Kilmarnock | Fa Cup | 2:1 | Yes | Yes |
| 10/26/05 | Hearts vs Kilmarnock | Premier League | 1:0 | No | No |
| 7/30/05 | Kilmarnock vs Hearts | Premier League | 2:4 | Yes | Yes |