Head to Head
| 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 |
Home History
| Scotland League Two | 2021/04/06 18:00 | FC Edinburgh v Annan Athletic | D | 1-1 |
| Scotland League Two | 2021/04/03 14:00 | Annan Athletic v Elgin | L | 0-3 |
| Scotland League Two | 2021/03/27 15:00 | Albion v Annan Athletic | D | 1-1 |
| Scotland FA Cup | 2021/03/23 19:45 | Formartine United v Annan Athletic | L | 4-2 |
| Scotland League Two | 2021/03/20 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2021/01/02 15:00 | Stranraer v Annan Athletic | L | 2-0 |
| Scotland FA Cup | 2020/12/26 15:00 | Gala Fairydean v Annan Athletic | W | 1-2 |
| Scotland League Two | 2020/12/22 19:45 | Brechin v Annan Athletic | D | 0-0 |
Away History
| Scotland League Two | 2021/04/06 18:00 | Stirling v Albion | D | 1-1 |
| Scotland League Two | 2021/04/03 14:00 | Queen's Park v Stirling | L | 1-0 |
| Scotland League Two | 2021/03/30 18:45 | Stirling v Stenhousemuir | W | 1-0 |
| Scotland League Two | 2021/03/27 15:00 | Elgin v Stirling | D | 1-1 |
| Scotland FA Cup | 2021/03/23 19:45 | Stirling v Raith | L | 0-2 |
| Scotland League Two | 2021/03/20 15:00 | Stirling v Brechin | W | 1-0 |
| Scotland FA Cup | 2020/12/26 15:00 | Berwick Rangers v Stirling | W | 0-3 |
| Scotland League Two | 2020/12/19 15:00 | FC Edinburgh v Stirling | W | 2-3 |