Head to Head
| 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 |
Home History
| Scotland FA Cup | 2022/01/22 15:00 | Clydebank v Annan Athletic | D | 2-2 |
| Scotland League Two | 2022/01/15 15:00 | Annan Athletic v Forfar | D | 2-2 |
| Scotland League Two | 2022/01/08 15:00 | Cowdenbeath v Annan Athletic | W | 1-3 |
| Scotland League Two | 2022/01/02 15:00 | Stranraer v Annan Athletic | D | 1-1 |
| Scotland League Two | 2021/12/26 13:00 | Annan Athletic v Kelty Hearts | W | 5-1 |
| Scotland League Two | 2021/12/18 15:00 | Stirling v Annan Athletic | W | 2-3 |
| Scotland League Two | 2021/12/11 15:00 | Annan Athletic v Elgin | W | 4-1 |
| Scotland League Two | 2021/12/03 19:45 | FC Edinburgh v Annan Athletic | W | 0-1 |
Away History
| Scotland FA Cup | 2022/01/21 19:45 | Rangers v Stirling | L | 4-0 |
| Scotland League Two | 2022/01/15 15:00 | Stranraer v Stirling | D | 3-3 |
| Scotland League Two | 2022/01/08 13:00 | Stirling v Kelty Hearts | L | 0-3 |
| Scotland League Two | 2022/01/02 15:00 | Stenhousemuir v Stirling | W | 1-2 |
| Scotland League Two | 2021/12/21 19:45 | Stirling v Elgin | L | 0-1 |
| Scotland League Two | 2021/12/18 15:00 | Stirling v Annan Athletic | L | 2-3 |
| Scotland League Two | 2021/12/11 15:00 | Forfar v Stirling | L | 2-0 |
| Scotland League Two | 2021/12/04 15:00 | Cowdenbeath v Stirling | L | 1-0 |