| 10. Round | 01/10/2000 | Heart of Midlothian | - | Motherwell FC | 3:0 |  |
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| 11. Round | 14/10/2000 | Dundee United | - | Heart of Midlothian | 0:4 |  |
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| 12. Round | 22/10/2000 | Hibernian FC | - | Heart of Midlothian | 6:2 | ||||
| 13. Round | 28/10/2000 | Heart of Midlothian | - | St. Johnstone FC | 0:3 |
Scotland