| 2008-07-27 15:00:0027 July 2008 | Alloa Athletic  | 4 - 1 |  Dundee | Challenge Cup | N/A | Report |
| 2008-08-02 15:00:002 August 2008 | Arbroath  | 4 - 1 | Alloa Athletic | League 1 | N/A | Report |
| 2008-08-02 19:45:002 August 2008 | Alloa Athletic | 2 - 0 |  Elgin City | Challenge Cup | N/A | Report |
| 2008-08-09 15:00:009 August 2008 | Alloa Athletic | 0 - 2 |  Ayr United | League 1 | N/A | Report |
| 2008-08-12 19:45:0012 August 2008 | Alloa Athletic | 0 - 2 |  Clyde | Challenge Cup | N/A | Report |
| 2008-08-16 15:00:0016 August 2008 | Alloa Athletic | 1 - 1 |  Raith Rovers | League 1 | N/A | Report |
| 2008-08-23 15:00:0023 August 2008 | Peterhead  | 1 - 0 | Alloa Athletic | League 1 | N/A | Report |
| 2008-08-26 19:45:0026 August 2008 | Dunfermline Athletic  | 1 - 0 | Alloa Athletic | League Cup | N/A | Report |
| 2008-08-30 15:00:0030 August 2008 | Alloa Athletic | 5 - 1 |  Stranraer | League 1 | N/A | Report |
| 2008-09-13 15:00:0013 September 2008 | Stirling Albion  | 3 - 2 | Alloa Athletic | League 1 | N/A | Report |
| 2008-09-20 15:00:0020 September 2008 | Alloa Athletic | 0 - 3 |  East Fife | League 1 | N/A | Report |
| 2008-09-27 15:00:0027 September 2008 | Queen’s Park  | 1 - 0 | Alloa Athletic | League 1 | N/A | Report |
| 2008-10-04 15:00:004 October 2008 | Brechin City  | 3 - 1 | Alloa Athletic | League 1 | N/A | Report |
| 2008-10-18 15:00:0018 October 2008 | Alloa Athletic | 2 - 1 | Arbroath | League 1 | N/A | Report |
| 2008-10-25 15:00:0025 October 2008 | Alloa Athletic | 1 - 0 | Peterhead | League 1 | N/A | Report |
| 2008-11-01 15:00:001 November 2008 | Raith Rovers | 4 - 1 | Alloa Athletic | League 1 | N/A | Report |
| 2008-11-08 15:00:008 November 2008 | Alloa Athletic | 4 - 3 | Stirling Albion | League 1 | N/A | Report |
| 2008-11-15 15:00:0015 November 2008 | Stranraer | 2 - 2 | Alloa Athletic | League 1 | N/A | Report |
| 2008-11-22 15:00:0022 November 2008 | Alloa Athletic | 1 - 3 | Queen’s Park | League 1 | N/A | Report |
| 2008-11-29 15:00:0029 November 2008 | Raith Rovers | 0 - 0 | Alloa Athletic | Scottish Cup | N/A | Report |
| 2008-12-06 15:00:006 December 2008 | East Fife | 1 - 0 | Alloa Athletic | League 1 | N/A | Report |
| 2008-12-09 19:45:009 December 2008 | Alloa Athletic | 2 - 1 | Raith Rovers | Scottish Cup | N/A | Report |
| 2008-12-13 15:00:0013 December 2008 | Ayr United | 3 - 0 | Alloa Athletic | League 1 | N/A | Report |
| 2008-12-20 15:00:0020 December 2008 | Alloa Athletic | 2 - 1 | Brechin City | League 1 | N/A | Report |
| 2008-12-27 15:00:0027 December 2008 | Alloa Athletic | 2 - 2 | Stranraer | League 1 | N/A | Report |
| 2009-01-10 15:00:0010 January 2009 | Alloa Athletic | 1 - 2 |  Aberdeen | Scottish Cup | N/A | Report |
| 2009-01-17 15:00:0017 January 2009 | Peterhead | 2 - 2 | Alloa Athletic | League 1 | N/A | Report |
| 2009-01-24 15:00:0024 January 2009 | Alloa Athletic | 0 - 0 | Raith Rovers | League 1 | N/A | Report |
| 2009-01-31 15:00:0031 January 2009 | Arbroath | 1 - 0 | Alloa Athletic | League 1 | N/A | Report |
| 2009-02-07 15:00:007 February 2009 | Alloa Athletic | 3 - 2 | Ayr United | League 1 | N/A | Report |
| 2009-02-14 15:00:0014 February 2009 | Queen’s Park | 1 - 2 | Alloa Athletic | League 1 | N/A | Report |
| 2009-02-21 15:00:0021 February 2009 | Alloa Athletic | 0 - 1 | East Fife | League 1 | N/A | Report |
| 2009-02-28 15:00:0028 February 2009 | Stranraer | 1 - 3 | Alloa Athletic | League 1 | N/A | Report |
| 2009-03-03 19:45:003 March 2009 | Stirling Albion | 0 - 0 | Alloa Athletic | League 1 | N/A | Report |
| 2009-03-07 15:00:007 March 2009 | Alloa Athletic | 2 - 3 | Stirling Albion | League 1 | N/A | Report |
| 2009-03-14 15:00:0014 March 2009 | Alloa Athletic | 2 - 0 | Arbroath | League 1 | N/A | Report |
| 2009-03-21 15:00:0021 March 2009 | Brechin City | 1 - 0 | Alloa Athletic | League 1 | N/A | Report |
| 2009-04-04 15:00:004 April 2009 | Alloa Athletic | 1 - 2 | Peterhead | League 1 | N/A | Report |
| 2009-04-11 15:00:0011 April 2009 | Raith Rovers | 3 - 1 | Alloa Athletic | League 1 | N/A | Report |
| 2009-04-18 15:00:0018 April 2009 | East Fife | 0 - 2 | Alloa Athletic | League 1 | N/A | Report |
| 2009-04-25 15:00:0025 April 2009 | Alloa Athletic | 0 - 0 | Queen’s Park | League 1 | N/A | Report |
| 2009-05-02 15:00:002 May 2009 | Ayr United | 1 - 1 | Alloa Athletic | League 1 | N/A | Report |
| 2009-05-09 15:00:009 May 2009 | Alloa Athletic | 3 - 2 | Brechin City | League 1 | N/A | Report |
Raith Rovers
Ayr United
Brechin City
Peterhead
Stirling Albion
East Fife
Arbroath
Alloa Athletic
Queen’s Park
Stranraer