| 4. Round | 24/08/2013 | Heart of Midlothian | - | Aberdeen FC | 2:1 |  |
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| 5. Round | 31/08/2013 | Inverness CT | - | Heart of Midlothian | 2:0 | ||||
| 8. Round | 28/09/2013 | Heart of Midlothian | - | Dundee United | 0:0 | ||||
| 9. Round | 05/10/2013 | Heart of Midlothian | - | St. Mirren FC | 0:2 | ||||
| 10. Round | 19/10/2013 | Motherwell FC | - | Heart of Midlothian | 2:1 | ||||
| 11. Round | 26/10/2013 | Kilmarnock FC | - | Heart of Midlothian | 2:0 | ||||
| 12. Round | 02/11/2013 | Heart of Midlothian | - | St. Johnstone FC | 0:2 | ||||
| 13. Round | 09/11/2013 | Aberdeen FC | - | Heart of Midlothian | 1:3 | ||||
| 14. Round | 23/11/2013 | Heart of Midlothian | - | Ross County FC | 2:2 | ||||
| 15. Round | 07/12/2013 | Dundee United | - | Heart of Midlothian | 4:1 | ||||
| 20. Round | 02/01/2014 | Hibernian FC | - | Heart of Midlothian | 2:1 | ||||
| 21. Round | 05/01/2014 | Heart of Midlothian | - | Partick Thistle | 0:2 | ||||
| 22. Round | 11/01/2014 | Heart of Midlothian | - | Motherwell FC | 0:1 | ||||
| 25. Round | 29/01/2014 | Heart of Midlothian | - | St. Mirren FC | 2:1 | ||||
| 26. Round | 15/02/2014 | Inverness CT | - | Heart of Midlothian | 0:0 | ||||
| 31. Round | 08/03/2014 | Kilmarnock FC | - | Heart of Midlothian | 4:2 |  |
Scotland