Head to Head
| Scotland League Two | 2023/04/22 14:00 | Stirling v Annan Athletic | L | 3-1 |
| Scotland League Two | 2023/02/18 15:00 | Annan Athletic v Stirling | D | 2-2 |
| Scotland League Two | 2022/11/12 15:00 | Stirling v Annan Athletic | W | 0-2 |
| Scotland League Two | 2022/08/20 14:00 | Annan Athletic v Stirling | L | 1-2 |
| Scotland League Two | 2022/03/19 15:00 | Stirling v Annan Athletic | W | 0-3 |
| Scotland League Two | 2022/01/29 15:30 | Annan Athletic v Stirling | D | 0-0 |
| Scotland League Two | 2021/12/18 15:00 | Stirling v Annan Athletic | W | 2-3 |
| Scotland League Two | 2021/08/14 14:00 | Annan Athletic v Stirling | W | 3-1 |
| Scotland League Two | 2021/04/10 14:00 | Annan Athletic v Stirling | L | 1-2 |
| Scotland League Two | 2020/10/31 15:00 | Stirling v Annan Athletic | L | 1-0 |
| Scotland League Two | 2020/01/18 15:00 | Annan Athletic v Stirling | L | 2-3 |
| Scotland League Two | 2019/11/16 15:00 | Stirling v Annan Athletic | L | 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 | 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 |
| Scotland League Two | 2017/03/18 15:00 | Stirling v Annan Athletic | L | 1-0 |
| Scotland League Two | 2017/01/28 15:00 | Annan Athletic v Stirling | W | 4-1 |
| Scotland League Two | 2016/12/17 15:00 | Stirling v Annan Athletic | L | 3-1 |
| Scotland League Two | 2016/08/06 14:00 | Annan Athletic v Stirling | W | 3-2 |
| 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 |