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| 23.09.2008 | 20:45 | Dundee United | - | Airdrie United FC | 2:0 | |
| 20:45 | Greenock Morton FC | - | Inverness CT | 1:2 n.V. | ||
| 20:45 | Falkirk FC | - | Queen Of The South | 2:1 | ||
| 20:45 | Celtic FC | - | Livingston FC | 4:0 | ||
| 20:45 | Dunfermline Athletic | - | St. Mirren FC | 2:0 | ||
| 24.09.2008 | 20:45 | Partick Thistle | - | Rangers FC | 1:2 n.V. | |
| 20:45 | Motherwell FC | - | Hamilton Academical | 1:2 n.V. | ||
| 20:45 | Kilmarnock FC | - | Aberdeen FC | 4:2 |
