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 | 2020/03/10 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 |
| Scotland League Two | 2020/02/15 15:00 | Cowdenbeath v Stirling | W | 1-4 |
| Scotland League Two | 2020/02/08 15:00 | Stirling v Queen's Park | L | 1-3 |
| Scotland League Two | 2020/02/01 15:00 | FC Edinburgh v Stirling | W | 0-1 |
| Scotland League Two | 2020/01/25 15:00 | Stirling v Elgin | L | 1-2 |
Away History
| 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 |
| Scotland League Two | 2020/02/08 15:00 | FC Edinburgh v Annan Athletic | L | 3-0 |
| Scotland League Two | 2020/02/01 15:00 | Annan Athletic v Stenhousemuir | L | 0-3 |
| Scotland League Two | 2020/01/25 15:00 | Cove Rangers v Annan Athletic | L | 2-0 |
| Scotland League Two | 2020/01/18 15:00 | Annan Athletic v Stirling | L | 2-3 |
| Scotland League Two | 2020/01/11 15:00 | Annan Athletic v Elgin | L | 0-4 |