Head to Head
| 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 |
| Scotland League Two | 2021/12/18 15:00 | Stirling v Annan Athletic | W | 2-3 |
| Scotland League Two | 2021/08/14 14:00 | Annan Athletic v Stirling | W | 3-1 |
Home History
| Scotland League Challenge Cup | 2023/09/09 14:00 | Annan Athletic v Peterhead | L | 0-2 |
| Scotland League One | 2023/09/02 14:00 | Kelty Hearts v Annan Athletic | D | 1-1 |
| Scotland League One | 2023/08/26 14:00 | Annan Athletic v FC Edinburgh | W | 3-2 |
| Scotland League One | 2023/08/19 14:00 | Queen of South v Annan Athletic | L | 3-1 |
| Scotland League Challenge Cup | 2023/08/15 18:45 | Annan Athletic v Stranraer | W | 3-1 |
| Scotland League One | 2023/08/12 14:00 | Annan Athletic v Montrose | L | 1-3 |
| Scotland League One | 2023/08/05 14:00 | Falkirk v Annan Athletic | L | 3-0 |
| Scotland League Cup | 2023/07/29 14:00 | Annan Athletic v Raith | L | 2-3 |
Away History
| Scotland League One | 2023/09/02 14:00 | Stirling v Hamilton | D | 2-2 |
| Scotland League One | 2023/08/26 14:00 | Stirling v Kelty Hearts | W | 1-0 |
| Scotland League One | 2023/08/22 18:45 | Falkirk v Stirling | L | 3-0 |
| Scotland League Cup | 2023/08/18 18:45 | Stirling v Aberdeen | L | 1-2 |
| Scotland League Challenge Cup | 2023/08/15 18:45 | Stirling v East Kilbride | L | 0-3 |
| Scotland League One | 2023/08/12 14:00 | Alloa v Stirling | W | 0-1 |
| Scotland League One | 2023/08/05 14:00 | Stirling v FC Edinburgh | W | 1-0 |
| Scotland League Cup | 2023/07/29 14:00 | St Johnstone v Stirling | W | 0-4 |