Head to Head
| Scotland League Two | 2016/04/23 14:00 | Stirling v Annan Athletic | L | 2-1 |
| Scotland League Two | 2016/02/27 15:00 | Annan Athletic v Stirling | D | 2-2 |
| Scotland League Two | 2015/12/19 15:00 | Stirling v Annan Athletic | L | 1-0 |
| Scotland League Two | 2015/08/15 14:00 | Annan Athletic v Stirling | D | 1-1 |
| Scotland League One Play-Offs | 2014/05/10 14:00 | Annan Athletic v Stirling | L | 3-5 |
| Scotland League One Play-Offs | 2014/05/07 18:45 | Stirling v Annan Athletic | L | 3-1 |
Home History
| Scotland League Challenge Cup | 2016/08/02 18:45 | Celtic U20 v Annan Athletic | L | 5-1 |
| Scotland League Cup | 2016/07/30 14:00 | East Stirlingshire v Annan Athletic | W | 0-2 |
| 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 |
| Europe Friendlies | 2016/07/12 18:45 | Annan Athletic v Queen of South | L | 0-4 |
| Europe 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 |
Away History
| Scotland League Challenge Cup | 2016/08/02 18:45 | Stirling v Hearts U20 | L | 2-3 |
| Scotland League Cup | 2016/07/30 14:00 | St Johnstone v Stirling | L | 4-0 |
| Scotland League Cup | 2016/07/26 18:45 | Stirling v Elgin | W | 4-1 |
| Scotland League Cup | 2016/07/19 18:45 | Brechin v Stirling | L | 2-1 |
| Scotland League Cup | 2016/07/16 14:00 | Stirling v Falkirk | W | 1-0 |
| Europe Friendlies | 2016/07/11 19:00 | Cumbernauld Colts v Stirling | W | 1-3 |
| Scotland League Two | 2016/04/30 14:00 | Clyde v Stirling | L | 3-1 |
| Scotland League Two | 2016/04/23 14:00 | Stirling v Annan Athletic | W | 2-1 |