Home History
| Scotland League Two | 2014/09/13 14:00 | East Stirlingshire v Clyde | W | 1-0 |
| Scotland League Two | 2014/08/30 14:00 | East Fife v East Stirlingshire | L | 3-1 |
| Scotland League Two | 2014/08/23 14:00 | Berwick Rangers v East Stirlingshire | L | 5-0 |
| Scotland League Two | 2014/08/16 14:00 | East Stirlingshire v Elgin | W | 2-1 |
| Scotland League Two | 2014/08/09 14:00 | Montrose v East Stirlingshire | L | 4-1 |
| Scotland League Cup | 2014/08/02 14:00 | East Stirlingshire v Ayr | L | 0-4 |
| Scotland League Challenge Cup | 2014/07/26 14:00 | East Stirlingshire v Falkirk | L | 1-7 |
Away History
| Scotland League Two | 2014/09/13 14:00 | Annan Athletic v Berwick Rangers | W | 2-0 |
| Scotland League Two | 2014/08/30 14:00 | Annan Athletic v Elgin | D | 3-3 |
| Scotland League Two | 2014/08/23 14:00 | Montrose v Annan Athletic | L | 2-0 |
| Scotland League Two | 2014/08/16 14:00 | Annan Athletic v Queen's Park | L | 0-1 |
| Scotland League Two | 2014/08/09 14:00 | Albion v Annan Athletic | L | 2-1 |
| Scotland League Cup | 2014/08/02 14:00 | Dunfermline v Annan Athletic | L | 5-1 |
| Club Friendly List | 2014/07/29 18:30 | Annan Athletic v Blackburn U23 | L | 0-5 |
| Scotland League Challenge Cup | 2014/07/26 14:00 | Hearts v Annan Athletic | L | 3-1 |