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| 29.11.2008 | 16:00 | Stirling Albion FC | - | Partick Thistle | 2:3 | |
| 16:00 | East Stirlingshire FC | - | Livingston FC | 2:1 | ||
| 16:00 | Albion Rovers | - | Queen's Park FC | 1:2 | ||
| 16:00 | East Fife FC | - | Arbroath FC | 2:0 | ||
| 16:00 | Peterhead FC | - | Greenock Morton FC | 2:1 | ||
| 16:00 | Clyde FC | - | Montrose FC | 2:0 | ||
| 16:00 | Airdrie United FC | - | Cove Rangers | 3:0 | ||
| 16:00 | Raith Rovers | - | Alloa Athletic | 0:0 | ||
| 16:00 | Clachnacuddin FC | - | Stenhousemuir FC | 0:5 | ||
| 16:00 | Ross County FC | - | Dumbarton FC | 2:2 | ||
| 06.12.2008 | 16:00 | Forres Mechanics FC | - | Dalbeattie Star | 2:2 | |
| 08.12.2008 | 20:45 | Edinburgh City FC | - | Brechin City FC | 0:3 | |
| 13.12.2008 | 16:00 | Inverurie Loco Works | - | Vale of Leithen FC | 4:0 | |
| 15.12.2008 | 20:45 | Forfar Athletic | - | Stranraer FC | 2:0 | |
| 20:45 | Elgin City | - | The Spartans FC | 1:2 | ||
| 17.12.2008 | 14:45 | Lochee United FC | - | Ayr United | 1:1 | |
| Entscheidungsspiele | ||||||
|---|---|---|---|---|---|---|
| 09.12.2008 | 20:45 | Alloa Athletic | - | Raith Rovers | 2:1 | |
| 15.12.2008 | 14:00 | Dalbeattie Star | - | Forres Mechanics FC | 2:4 n.V. | |
| 20:45 | Dumbarton FC | - | Ross County FC | 1:2 | ||
| 23.12.2008 | 20:45 | Ayr United | - | Lochee United FC | 3:1 | |
