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| 10.01.2009 | 16:00 | Peterhead FC | - | Queen's Park FC | 2:2 | |
| 16:00 | Alloa Athletic | - | Aberdeen FC | 1:2 | ||
| 16:00 | Falkirk FC | - | Queen Of The South | 4:2 | ||
| 16:00 | Airdrie United FC | - | The Spartans FC | 2:1 | ||
| 16:00 | Ross County FC | - | Hamilton Academical | 0:1 | ||
| 16:00 | Inverness CT | - | Partick Thistle | 3:0 | ||
| 16:00 | Celtic FC | - | Dundee FC | 2:1 | ||
| 16:00 | Stenhousemuir FC | - | East Fife FC | 0:1 | ||
| 16:00 | Ayr United | - | Kilmarnock FC | 2:2 | ||
| 16:00 | Dunfermline Athletic | - | Clyde FC | 2:0 | ||
| 11.01.2009 | 13:15 | Hibernian FC | - | Heart of Midlothian | 0:2 | |
| 16:00 | East Stirlingshire FC | - | Dundee United | 0:4 | ||
| 13.01.2009 | 20:45 | Brechin City FC | - | St. Mirren FC | 1:3 | |
| 20:45 | Forfar Athletic | - | Forres Mechanics FC | 6:1 | ||
| 21:05 | St. Johnstone FC | - | Rangers FC | 0:2 | ||
| 02.02.2009 | 20:45 | Inverurie Loco Works | - | Motherwell FC | 0:3 | |
| Entscheidungsspiele | ||||||
|---|---|---|---|---|---|---|
| 20.01.2009 | 20:45 | Queen's Park FC | - | Peterhead FC | 1:0 | |
| 22.01.2009 | 20:30 | Kilmarnock FC | - | Ayr United | 3:1 | |
