Head to Head
| 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 | W | 3-0 |
| Scotland League Two | 2023/04/22 14:00 | Stirling v Annan Athletic | L | 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 | W | 0-2 |
| Scotland League Two | 2022/08/20 14:00 | Annan Athletic v Stirling | L | 1-2 |
| Scotland League Two | 2022/03/19 15:00 | Stirling v Annan Athletic | W | 0-3 |
| Scotland League Two | 2022/01/29 15:30 | Annan Athletic v Stirling | D | 0-0 |
Home History
| Scotland League One | 2024/02/13 19:45 | Alloa v Annan Athletic | L | 2-1 |
| Scotland League One | 2024/02/10 15:00 | Hamilton v Annan Athletic | W | 2-3 |
| Scotland League One | 2024/02/03 15:00 | Annan Athletic v Alloa | L | 2-3 |
| Scotland League One | 2024/01/27 15:00 | Annan Athletic v FC Edinburgh | W | 3-0 |
| Scotland League One | 2024/01/13 15:00 | Kelty Hearts v Annan Athletic | D | 1-1 |
| Scotland League One | 2024/01/06 15:00 | Annan Athletic v Montrose | D | 2-2 |
| Scotland League One | 2023/12/30 15:00 | Queen of South v Annan Athletic | L | 2-1 |
| Scotland League One | 2023/12/23 15:00 | Annan Athletic v Falkirk | L | 0-3 |
Away History
| Scotland League One | 2024/02/10 15:00 | Alloa v Stirling | L | 1-0 |
| Scotland League One | 2024/02/06 19:45 | Stirling v Montrose | L | 0-2 |
| Scotland League One | 2024/02/03 15:00 | Stirling v Cove Rangers | D | 2-2 |
| Scotland League One | 2024/01/27 15:00 | Stirling v Kelty Hearts | W | 5-0 |
| Scotland League One | 2024/01/13 15:00 | Montrose v Stirling | W | 0-1 |
| Scotland League One | 2023/12/30 15:00 | Falkirk v Stirling | L | 5-0 |
| Scotland League One | 2023/12/23 15:00 | Stirling v Queen of South | D | 1-1 |
| Scotland League One | 2023/12/16 15:00 | Stirling v Annan Athletic | D | 1-1 |