| 2008-07-27 15:00:0027 July 2008 | Alloa Athletic    | 4 - 1 |   Dundee | Challenge Cup | N/A | |
| 2008-08-02 15:00:002 August 2008 | Arbroath   | 4 - 1 | Alloa Athletic | League 1 | N/A | |
| 2008-08-02 19:45:002 August 2008 | Alloa Athletic | 2 - 0 |  Elgin City | Challenge Cup | N/A | |
| 2008-08-09 15:00:009 August 2008 | Alloa Athletic | 0 - 2 |  Ayr United | League 1 | N/A | |
| 2008-08-12 19:45:0012 August 2008 | Alloa Athletic | 0 - 2 |  Clyde | Challenge Cup | N/A | |
| 2008-08-16 15:00:0016 August 2008 | Alloa Athletic | 1 - 1 |   Raith Rovers | League 1 | N/A | |
| 2008-08-23 15:00:0023 August 2008 | Peterhead  | 1 - 0 | Alloa Athletic | League 1 | N/A | |
| 2008-08-26 19:45:0026 August 2008 | Dunfermline Athletic   | 1 - 0 | Alloa Athletic | League Cup | N/A | |
| 2008-08-30 15:00:0030 August 2008 | Alloa Athletic | 5 - 1 |  Stranraer | League 1 | N/A | |
| 2008-09-13 15:00:0013 September 2008 | Stirling Albion  | 3 - 2 | Alloa Athletic | League 1 | N/A | |
| 2008-09-20 15:00:0020 September 2008 | Alloa Athletic | 0 - 3 |   East Fife | League 1 | N/A | |
| 2008-09-27 15:00:0027 September 2008 | Queen’s Park   | 1 - 0 | Alloa Athletic | League 1 | N/A | |
| 2008-10-04 15:00:004 October 2008 | Brechin City  | 3 - 1 | Alloa Athletic | League 1 | N/A | |
| 2008-10-18 15:00:0018 October 2008 | Alloa Athletic | 2 - 1 | Arbroath | League 1 | N/A | |
| 2008-10-25 15:00:0025 October 2008 | Alloa Athletic | 1 - 0 | Peterhead | League 1 | N/A | |
| 2008-11-01 15:00:001 November 2008 | Raith Rovers | 4 - 1 | Alloa Athletic | League 1 | N/A | |
| 2008-11-08 15:00:008 November 2008 | Alloa Athletic | 4 - 3 | Stirling Albion | League 1 | N/A | |
