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| 22/09/2009 | 19:45 | Motherwell FC | - | Inverness CT | 3:2 aet | |
| 19:45 | Dundee FC | - | Aberdeen FC | 3:2 aet | ||
| 19:45 | Hibernian FC | - | St. Johnstone FC | 1:3 | ||
| 19:45 | Kilmarnock FC | - | St. Mirren FC | 1:2 | ||
| 19:45 | Ross County FC | - | Dundee United | 0:2 | ||
| 23/09/2009 | 19:35 | Queen Of The South | - | Rangers FC | 1:2 | |
| 19:45 | Falkirk FC | - | Celtic FC | 0:4 | ||
| 19:45 | Heart of Midlothian | - | Dunfermline Athletic | 2:1 |
