Head to Head
| Scotland League Two | 2020/01/18 15:00 | Annan Athletic v Stirling | W | 2-3 |
| Scotland League Two | 2019/11/16 15:00 | Stirling v Annan Athletic | W | 2-0 |
| Scotland League Two | 2019/09/21 14:00 | Annan Athletic v Stirling | D | 0-0 |
| 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 | W | 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 | L | 1-2 |
| Scotland League Two | 2018/04/21 14:00 | Annan Athletic v Stirling | L | 3-1 |
Home History
| Scotland League Two | 2020/10/24 14:00 | Stenhousemuir v Stirling | D | 2-2 |
| Scotland League Two | 2020/10/17 14:00 | Stirling v Queen's Park | D | 0-0 |
| Scotland League Cup | 2020/10/10 14:00 | Elgin v Stirling | L | 2-0 |
| Scotland League Cup | 2020/10/06 18:45 | Stirling v Arbroath | L | 1-2 |
| Scotland League Two | 2020/03/10 19:45 | Stirling v Cove Rangers | L | 1-7 |
| Scotland League Two | 2020/03/07 15:00 | Elgin v Stirling | L | 3-1 |
| Scotland League Two | 2020/03/03 19:45 | Stirling v Stenhousemuir | D | 0-0 |
| Scotland League Two | 2020/02/29 15:00 | Brechin v Stirling | W | 0-2 |
Away History
| Scotland League Two | 2020/10/24 14:00 | Annan Athletic v Stranraer | D | 1-1 |
| Scotland League Two | 2020/10/17 14:00 | Cowdenbeath v Annan Athletic | W | 0-3 |
| Scotland League Cup | 2020/10/13 18:45 | Ayr v Annan Athletic | L | 1-0 |
| Scotland League Cup | 2020/10/10 14:00 | Annan Athletic v Stranraer | L | 5-6 |
| Scotland League Cup | 2020/10/06 18:45 | Annan Athletic v Hamilton | W | 3-1 |
| Scotland League Two | 2020/03/07 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2020/02/29 15:00 | Queen's Park v Annan Athletic | L | 2-0 |
| Scotland League Two | 2020/02/22 15:00 | Annan Athletic v Albion | W | 2-1 |