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 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 |
| Scotland League Two | 2020/12/19 15:00 | Annan Athletic v Queen's Park | L | 1-2 |
| Scotland League Two | 2020/12/05 15:00 | Elgin v Annan Athletic | L | 1-0 |
| Scotland League Two | 2020/11/28 15:00 | Annan Athletic v FC Edinburgh | L | 0-4 |
| Scotland League Two | 2020/11/21 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Scotland League Cup | 2020/11/10 19:45 | Albion v Annan Athletic | W | 1-5 |
| Scotland League Two | 2020/11/07 15:00 | Annan Athletic v Albion | L | 2-3 |
Away History
| 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 |
| Scotland League Two | 2020/12/12 15:00 | Stirling v Cowdenbeath | W | 1-0 |
| Scotland League Two | 2020/12/05 15:00 | Stranraer v Stirling | D | 2-2 |
| Scotland League Two | 2020/11/28 15:00 | Albion v Stirling | W | 0-1 |
| Scotland League Two | 2020/11/21 15:00 | Stirling v Elgin | L | 1-2 |
| Scotland League Cup | 2020/11/14 15:00 | Ross County v Stirling | L | 3-0 |
| Scotland League Cup | 2020/11/10 19:45 | Stirling v Montrose | W | 2-1 |