Head to Head
| 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 |
| Scotland League Two | 2021/08/14 14:00 | Annan Athletic v Stirling | L | 3-1 |
Home History
| Scotland League Cup | 2023/07/18 18:45 | Alloa v Stirling | W | 1-2 |
| Scotland League Cup | 2023/07/15 14:00 | Stirling v Ayr | D | 1-1 |
| UK Friendlies | 2023/07/04 18:45 | Civil Service Strollers v Stirling | W | 0-5 |
| Scotland League Two | 2023/05/06 14:00 | Albion v Stirling | L | 2-0 |
| Scotland League Two | 2023/04/29 14:00 | Stirling v Forfar | W | 2-1 |
| Scotland League Two | 2023/04/22 14:00 | Stirling v Annan Athletic | W | 3-1 |
| Scotland League Two | 2023/04/18 18:45 | Dumbarton v Stirling | D | 0-0 |
| Scotland League Two | 2023/04/15 14:00 | Stenhousemuir v Stirling | W | 0-1 |
Away History
| Scotland League Cup | 2023/07/18 18:45 | Dunfermline v Annan Athletic | L | 4-0 |
| Scotland League Cup | 2023/07/15 14:00 | Kilmarnock v Annan Athletic | L | 3-0 |
| Scotland League One Play-Offs | 2023/05/19 18:35 | Clyde v Annan Athletic | W | 1-2 |
| Scotland League One Play-Offs | 2023/05/16 18:35 | Annan Athletic v Clyde | W | 3-1 |
| Scotland League One Play-Offs | 2023/05/13 14:00 | Dumbarton v Annan Athletic | D | 0-0 |
| Scotland League One Play-Offs | 2023/05/09 18:45 | Annan Athletic v Dumbarton | W | 6-0 |
| Scotland League Two | 2023/05/06 14:00 | Stenhousemuir v Annan Athletic | L | 2-1 |
| Scotland League Two | 2023/04/29 14:00 | Annan Athletic v Bonnyrigg Rose | D | 0-0 |
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