Head to Head
| Scotland League Two | 2016/04/16 14:00 | Annan Athletic v East Stirlingshire | W | 1-3 |
| Scotland League Two | 2016/02/20 15:00 | East Stirlingshire v Annan Athletic | L | 0-1 |
| Scotland League Two | 2015/12/12 15:00 | Annan Athletic v East Stirlingshire | L | 3-1 |
| Scotland League Two | 2015/08/22 14:00 | East Stirlingshire v Annan Athletic | W | 3-1 |
| Scotland League Two | 2015/03/21 15:00 | Annan Athletic v East Stirlingshire | L | 3-2 |
| Scotland League Two | 2015/01/17 15:00 | East Stirlingshire v Annan Athletic | L | 1-3 |
| Scotland League Two | 2014/10/25 14:00 | Annan Athletic v East Stirlingshire | L | 4-3 |
| Scotland League Two | 2014/09/20 14:00 | East Stirlingshire v Annan Athletic | L | 0-1 |
Home History
| Scotland League Cup | 2016/07/26 18:45 | Motherwell v East Stirlingshire | L | 3-0 |
| Scotland League Cup | 2016/07/22 18:45 | East Stirlingshire v Rangers | L | 0-3 |
| Scotland League Cup | 2016/07/19 18:45 | Stranraer v East Stirlingshire | L | 3-1 |
| Scotland League Two | 2016/05/14 14:00 | East Stirlingshire v FC Edinburgh | L | 0-1 |
| Scotland League Two | 2016/05/07 14:00 | FC Edinburgh v East Stirlingshire | D | 1-1 |
| Scotland League Two | 2016/04/30 14:00 | East Fife v East Stirlingshire | D | 1-1 |
| Scotland League Two | 2016/04/23 14:00 | East Stirlingshire v Elgin | L | 0-3 |
| Scotland League Two | 2016/04/16 14:00 | Annan Athletic v East Stirlingshire | W | 1-3 |
Away History
| Scotland League Cup | 2016/07/23 14:00 | Annan Athletic v Motherwell | L | 1-3 |
| Scotland League Cup | 2016/07/19 18:45 | Rangers v Annan Athletic | L | 2-0 |
| Scotland League Cup | 2016/07/16 14:00 | Annan Athletic v Stranraer | L | 1-2 |
| World Club Friendlies | 2016/07/12 18:45 | Annan Athletic v Queen of South | L | 0-4 |
| World Club Friendlies | 2016/07/02 14:00 | Crusaders v Annan Athletic | D | 2-2 |
| Scotland League Two | 2016/04/30 14:00 | Annan Athletic v Queen's Park | W | 1-0 |
| Scotland League Two | 2016/04/23 14:00 | Stirling v Annan Athletic | L | 2-1 |
| Scotland League Two | 2016/04/16 14:00 | Annan Athletic v East Stirlingshire | L | 1-3 |