| 2. Round | 17/08/2003 | Hibernian FC | - | Heart of Midlothian | 1:0 |  |
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| 3. Round | 23/08/2003 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 4. Round | 31/08/2003 | Dunfermline Athletic | - | Heart of Midlothian | 0:1 | ||||
| 5. Round | 13/09/2003 | Kilmarnock FC | - | Heart of Midlothian | 0:2 | |
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| 33. Round | 17/04/2004 | Heart of Midlothian | - | Livingston FC | 1:1 |
Scotland