Head to Head
| Scotland League Two | 2025/08/09 14:00 | Stirling v Annan Athletic | D | 0-0 |
| Scotland League One | 2024/05/04 14:00 | Stirling v Annan Athletic | D | 1-1 |
| 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 |
Home History
| Scotland League Challenge Cup | 2025/10/11 14:00 | Stirling v Dundee B | W | 2-0 |
| Scotland League Two | 2025/10/04 14:00 | Stirling v Dumbarton | D | 2-2 |
| Scotland League Two | 2025/09/27 14:00 | Stirling v Clyde | L | 2-4 |
| Scotland League Challenge Cup | 2025/09/23 18:45 | Stirling v Montrose | L | 1-2 |
| Scotland League Two | 2025/09/20 14:00 | Spartans v Stirling | W | 1-3 |
| Scotland League Two | 2025/09/13 14:00 | Elgin v Stirling | L | 3-0 |
| Scotland League Challenge Cup | 2025/09/05 19:00 | Inverness CT v Stirling | L | 2-1 |
| Scotland League Two | 2025/08/30 14:00 | Stirling v Stranraer | W | 1-0 |
Away History
| Scotland League Challenge Cup | 2025/10/11 14:00 | Hamilton v Annan Athletic | W | 1-2 |
| Scotland League Two | 2025/10/04 14:00 | Stranraer v Annan Athletic | W | 0-1 |
| Scotland League Two | 2025/09/27 14:00 | Annan Athletic v East Kilbride | W | 3-1 |
| Scotland League Challenge Cup | 2025/09/23 18:45 | Annan Athletic v Rangers B | W | 4-3 |
| Scotland League Two | 2025/09/20 14:00 | Forfar v Annan Athletic | L | 1-0 |
| Scotland League Two | 2025/09/13 14:00 | Annan Athletic v Clyde | L | 0-6 |
| Scotland League Challenge Cup | 2025/09/06 14:00 | Annan Athletic v St Mirren B | D | 2-2 |
| Scotland League Two | 2025/08/30 14:00 | Spartans v Annan Athletic | L | 1-0 |