Head to Head
| Schottland - League 2 | 2021/04/10 14:00 | Annan Athletic v Stirling | L | 1-2 |
| Schottland - League 2 | 2020/10/31 15:00 | Stirling v Annan Athletic | L | 1-0 |
| Schottland - League 2 | 2020/01/18 15:00 | Annan Athletic v Stirling | L | 2-3 |
| Schottland - League 2 | 2019/11/16 15:00 | Stirling v Annan Athletic | L | 2-0 |
| Schottland - League 2 | 2019/09/21 14:00 | Annan Athletic v Stirling | D | 0-0 |
| Schottland - League 2 | 2019/04/13 14:00 | Annan Athletic v Stirling | D | 2-2 |
| Schottland - League 2 | 2019/01/12 15:00 | Stirling v Annan Athletic | L | 2-1 |
| Schottland - League 2 | 2018/11/17 15:00 | Annan Athletic v Stirling | D | 2-2 |
Home History
| Schottland - League Challenge Cup | 2021/08/11 18:45 | Celtic B v Annan Athletic | L | 2-0 |
| Schottland - League 2 | 2021/08/07 14:00 | Stranraer v Annan Athletic | W | 0-3 |
| Schottland - League 2 | 2021/07/31 14:00 | Annan Athletic v Forfar | L | 0-2 |
| Schottland - Ligapokal | 2021/07/24 14:00 | Motherwell v Annan Athletic | L | 2-0 |
| Schottland - Ligapokal | 2021/07/20 18:45 | Annan Athletic v Queen's Park | L | 1-2 |
| Schottland - Ligapokal | 2021/07/13 18:45 | Annan Athletic v Queen of South | L | 1-3 |
| Schottland - Ligapokal | 2021/07/10 14:00 | Airdrieonians v Annan Athletic | W | 5-6 |
| Schottland - League 2 | 2021/05/01 14:00 | Annan Athletic v Cowdenbeath | D | 1-1 |
Away History
| Schottland - League 2 | 2021/08/07 14:00 | Stirling v Kelty Hearts | L | 1-3 |
| Schottland - League 2 | 2021/07/31 14:00 | Stenhousemuir v Stirling | W | 0-1 |
| Schottland - Ligapokal | 2021/07/24 14:00 | Stirling v Peterhead | W | 3-1 |
| Schottland - Ligapokal | 2021/07/20 18:45 | Stirling v Hearts | L | 0-2 |
| Schottland - Ligapokal | 2021/07/17 14:00 | Inverness CT v Stirling | W | 4-5 |
| Schottland - Ligapokal | 2021/07/10 14:00 | Cove Rangers v Stirling | W | 2-3 |
| Schottland - League 2 | 2021/05/01 14:00 | Stirling v Stranraer | D | 2-2 |
| Schottland - League 2 | 2021/04/29 18:00 | Elgin v Stirling | L | 3-1 |