Head to Head
| Scotland League One | 2024/02/17 15:00 | Annan Athletic v Stirling | L | 2-1 |
| Scotland League One | 2023/12/16 15:00 | Stirling v Annan Athletic | D | 1-1 |
| Scotland League One | 2023/09/16 14:00 | Annan Athletic v Stirling | L | 3-0 |
| Scotland League Two | 2023/04/22 14:00 | Stirling v Annan Athletic | W | 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 | L | 0-2 |
| Scotland League Two | 2022/08/20 14:00 | Annan Athletic v Stirling | W | 1-2 |
| Scotland League Two | 2022/03/19 15:00 | Stirling v Annan Athletic | L | 0-3 |
Home History
| Scotland League One | 2024/04/27 14:00 | FC Edinburgh v Stirling | W | 1-3 |
| Scotland League One | 2024/04/20 14:00 | Stirling v Queen of South | D | 0-0 |
| Scotland League One | 2024/04/13 14:00 | Kelty Hearts v Stirling | L | 1-0 |
| Scotland League One | 2024/04/06 14:00 | Stirling v Alloa | L | 1-5 |
| Scotland League One | 2024/03/30 15:00 | Cove Rangers v Stirling | L | 4-2 |
| Scotland League One | 2024/03/23 15:00 | Stirling v Montrose | W | 1-0 |
| Scotland League One | 2024/03/16 15:00 | Hamilton v Stirling | L | 3-0 |
| Scotland League One | 2024/03/09 15:00 | Stirling v Falkirk | L | 1-2 |
Away History
| Scotland League One | 2024/04/27 14:00 | Annan Athletic v Falkirk | D | 3-3 |
| Scotland League One | 2024/04/20 14:00 | FC Edinburgh v Annan Athletic | W | 1-2 |
| Scotland League One | 2024/04/13 14:00 | Annan Athletic v Cove Rangers | W | 4-2 |
| Scotland League One | 2024/04/06 14:00 | Annan Athletic v Hamilton | L | 1-3 |
| Scotland League One | 2024/03/30 15:00 | Alloa v Annan Athletic | D | 1-1 |
| Scotland League One | 2024/03/23 15:00 | Annan Athletic v Kelty Hearts | W | 3-2 |
| Scotland League One | 2024/03/16 15:00 | Montrose v Annan Athletic | D | 1-1 |
| Scotland League One | 2024/03/09 15:00 | Annan Athletic v Queen of South | W | 2-1 |