5. Round | 30/08/2008 | Airdrie United FC | - | Greenock Morton FC | 5:0 | ||||
11. Round | 04/11/2008 | Airdrie United FC | - | Dunfermline Athletic | 1:3 | ||||
22. Round | 24/01/2009 | Airdrie United FC | - | Dundee FC | 1:0 | ||||
25. Round | 22/02/2009 | Airdrie United FC | - | Clyde FC | 1:0 | ||||
27. Round | 07/03/2009 | Airdrie United FC | - | Livingston FC | 4:4 |