| 1. Round | 07/08/2016 | Heart of Midlothian | - | Celtic FC | 1:2 | ||||
| 2. Round | 13/08/2016 | Aberdeen FC | - | Heart of Midlothian | 0:0 | ||||
| 3. Round | 20/08/2016 | Heart of Midlothian | - | Inverness CT | 5:1 |  |
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| 4. Round | 27/08/2016 | Partick Thistle | - | Heart of Midlothian | 1:2 | ||||
| 5. Round | 10/09/2016 | Heart of Midlothian | - | Hamilton Academical | 3:1 | |
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| 6. Round | 17/09/2016 | St. Johnstone FC | - | Heart of Midlothian | 1:0 | ||||
| 7. Round | 24/09/2016 | Heart of Midlothian | - | Ross County FC | 0:0 | ||||
| 8. Round | 30/09/2016 | Motherwell FC | - | Heart of Midlothian | 1:3 | |
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| 22. Round | 29/01/2017 | Celtic FC | - | Heart of Midlothian | 4:0 | ||||
| 23. Round | 01/02/2017 | Heart of Midlothian | - | Rangers FC | 4:1 | ||||
| 24. Round | 04/02/2017 | Motherwell FC | - | Heart of Midlothian | 0:3 | ||||
| 26. Round | 25/02/2017 | Partick Thistle | - | Heart of Midlothian | 2:0 |  |
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| 27. Round | 01/03/2017 | Heart of Midlothian | - | Ross County FC | 0:1 | ||||
| 28. Round | 11/03/2017 | Heart of Midlothian | - | Hamilton Academical | 4:0 | ||||
| 29. Round | 18/03/2017 | Aberdeen FC | - | Heart of Midlothian | 2:0 | ||||
| 31. Round | 05/04/2017 | St. Johnstone FC | - | Heart of Midlothian | 1:0 |  |
Scotland