Head to Head
| Scotland League Two | 2019/04/13 14:00 | Annan Athletic v Stirling | D | 2-2 |
| Scotland League Two | 2019/01/12 15:00 | Stirling v Annan Athletic | L | 2-1 |
| Scotland League Two | 2018/11/17 15:00 | Annan Athletic v Stirling | D | 2-2 |
| Scotland League Two | 2018/09/22 14:00 | Stirling v Annan Athletic | W | 1-2 |
| Scotland League Two | 2018/04/21 14:00 | Annan Athletic v Stirling | W | 3-1 |
| Scotland League Two | 2018/02/17 15:00 | Stirling v Annan Athletic | L | 3-0 |
| Scotland League Two | 2017/12/16 15:00 | Annan Athletic v Stirling | D | 1-1 |
| Scotland League Two | 2017/09/23 14:00 | Stirling v Annan Athletic | L | 3-2 |
Home History
| Scotland League Two | 2019/08/17 14:00 | Annan Athletic v Albion | W | 3-2 |
| Scotland League Challenge Cup | 2019/08/13 18:45 | Annan Athletic v Kelty Hearts | L | 6-7 |
| Scotland League Two | 2019/08/10 14:00 | Annan Athletic v Elgin | D | 1-1 |
| Scotland League Two | 2019/08/03 14:00 | Brechin v Annan Athletic | W | 0-1 |
| Scotland League Cup | 2019/07/27 14:00 | Motherwell v Annan Athletic | L | 4-0 |
| Scotland League Cup | 2019/07/23 18:45 | Annan Athletic v Morton | L | 0-5 |
| Scotland League Cup | 2019/07/16 18:45 | Queen of South v Annan Athletic | L | 8-7 |
| Scotland League Cup | 2019/07/13 14:00 | Annan Athletic v Dumbarton | L | 0-1 |
Away History
| Scotland League Two | 2019/08/17 14:00 | FC Edinburgh v Stirling | L | 1-0 |
| Scotland League Challenge Cup | 2019/08/13 18:45 | East Fife v Stirling | W | 0-2 |
| Scotland League Two | 2019/08/10 14:00 | Cowdenbeath v Stirling | L | 1-0 |
| Scotland League Two | 2019/08/03 14:00 | Stirling v Queen's Park | L | 0-1 |
| Scotland League Cup | 2019/07/23 18:45 | Alloa v Stirling | L | 2-1 |
| Scotland League Cup | 2019/07/20 14:00 | Elgin v Stirling | L | 3-0 |
| Scotland League Cup | 2019/07/17 18:45 | Stirling v Arbroath | L | 1-6 |
| Scotland League Cup | 2019/07/13 14:00 | Stirling v Hibernian | L | 5-6 |