Head to Head
| 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 |
| Scotland League Two | 2022/01/29 15:30 | Annan Athletic v Stirling | D | 0-0 |
| Scotland League Two | 2021/12/18 15:00 | Stirling v Annan Athletic | L | 2-3 |
Home History
| Scotland League One | 2023/12/09 15:00 | FC Edinburgh v Stirling | W | 1-3 |
| Scotland FA Cup | 2023/11/25 15:00 | Stirling v Cove Rangers | L | 0-2 |
| Scotland League One | 2023/11/18 15:00 | Cove Rangers v Stirling | L | 3-1 |
| Scotland League One | 2023/11/11 15:00 | Hamilton v Stirling | L | 5-0 |
| Scotland League One | 2023/11/04 15:00 | Stirling v Alloa | L | 0-2 |
| Scotland League One | 2023/10/28 14:00 | Kelty Hearts v Stirling | L | 1-0 |
| Scotland League One | 2023/10/21 14:00 | Stirling v Falkirk | L | 1-2 |
| Scotland League One | 2023/10/07 14:00 | Queen of South v Stirling | W | 0-1 |
Away History
| Scotland League One | 2023/12/09 15:00 | Annan Athletic v Cove Rangers | L | 1-3 |
| Scotland League One | 2023/11/28 19:45 | Annan Athletic v Hamilton | L | 1-2 |
| Scotland FA Cup | 2023/11/25 15:00 | Annan Athletic v Dumbarton | L | 4-5 |
| Scotland League One | 2023/11/11 15:00 | Montrose v Annan Athletic | D | 1-1 |
| Scotland League One | 2023/11/04 15:00 | Annan Athletic v Kelty Hearts | D | 2-2 |
| Scotland League One | 2023/10/28 14:00 | FC Edinburgh v Annan Athletic | L | 3-2 |
| Scotland League One | 2023/10/21 14:00 | Annan Athletic v Queen of South | L | 0-1 |
| Scotland League One | 2023/10/07 14:00 | Cove Rangers v Annan Athletic | L | 3-2 |