29/11/2008 15:00 Stirling Albion FC - Partick Thistle 2:3
15:00 East Stirlingshire FC - Livingston FC 2:1
15:00 Albion Rovers - Queen's Park FC 1:2
15:00 East Fife FC - Arbroath FC 2:0
15:00 Peterhead FC - Greenock Morton FC 2:1
15:00 Clyde FC - Montrose FC 2:0
15:00 Airdrie United FC - Cove Rangers 3:0
15:00 Raith Rovers - Alloa Athletic 0:0
15:00 Clachnacuddin FC - Stenhousemuir FC 0:5
15:00 Ross County FC - Dumbarton FC 2:2
06/12/2008 15:00 Forres Mechanics FC - Dalbeattie Star 2:2
08/12/2008 19:45 Edinburgh City FC - Brechin City FC 0:3
13/12/2008 15:00 Inverurie Loco Works - Vale of Leithen FC 4:0
15/12/2008 19:45 Forfar Athletic - Stranraer FC 2:0
19:45 Elgin City - The Spartans FC 1:2
17/12/2008 13:45 Lochee United FC - Ayr United 1:1
decisive matches
09/12/2008 19:45 Alloa Athletic - Raith Rovers 2:1
15/12/2008 13:00 Dalbeattie Star - Forres Mechanics FC 2:4 aet
19:45 Dumbarton FC - Ross County FC 1:2
23/12/2008 19:45 Ayr United - Lochee United FC 3:1