Head to Head
| 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 |
| Scotland League Two | 2022/08/20 14:00 | Annan Athletic v Stirling | W | 1-2 |
Home History
| Scotland League Two | 2025/05/03 14:00 | Forfar v Stirling | D | 0-0 |
| Scotland League Two | 2025/04/26 14:00 | Stirling v Clyde | L | 1-4 |
| Scotland League Two | 2025/04/19 14:00 | East Fife v Stirling | L | 2-0 |
| Scotland League Two | 2025/04/12 14:00 | Stirling v Stranraer | W | 3-1 |
| Scotland League Two | 2025/04/05 14:00 | Elgin v Stirling | W | 0-2 |
| Scotland League Two | 2025/03/29 15:00 | Stirling v FC Edinburgh | W | 2-1 |
| Scotland League Two | 2025/03/22 15:00 | Stirling v Peterhead | L | 1-2 |
| Scotland League Two | 2025/03/15 15:00 | Bonnyrigg Rose v Stirling | D | 1-1 |
Away History
| Scotland League One Play-Offs | 2025/05/16 18:30 | Annan Athletic v East Fife | D | 1-1 |
| Scotland League One Play-Offs | 2025/05/13 18:30 | East Fife v Annan Athletic | L | 3-2 |
| Scotland League One Play-Offs | 2025/05/10 14:00 | Annan Athletic v Elgin | L | 1-2 |
| Scotland League One Play-Offs | 2025/05/06 18:45 | Elgin v Annan Athletic | W | 2-4 |
| Scotland League One | 2025/05/03 14:00 | Annan Athletic v Cove Rangers | L | 2-4 |
| Scotland League One | 2025/04/26 14:00 | Dumbarton v Annan Athletic | L | 3-1 |
| Scotland League One | 2025/04/19 14:00 | Annan Athletic v Arbroath | W | 5-1 |
| Scotland League One | 2025/04/12 14:00 | Alloa v Annan Athletic | L | 1-0 |
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