Head to Head
| Skottland - League Two | 2021/04/27 18:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
| Skottland - League Two | 2021/04/20 18:45 | Annan Athletic v Stenhousemuir | W | 5-1 |
| Skottland - League Two | 2020/11/21 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Skottland - League Two | 2020/02/01 15:00 | Annan Athletic v Stenhousemuir | L | 0-3 |
| Skottland - League Two | 2019/12/07 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Skottland - League Two | 2019/08/31 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
| Skottland - League One - Playoff | 2019/05/11 14:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Skottland - League One - Playoff | 2019/05/07 18:45 | Annan Athletic v Stenhousemuir | W | 2-0 |
Home History
| Skottland - League Two | 2021/08/28 14:00 | Cowdenbeath v Annan Athletic | W | 1-3 |
| Skottland - League Two | 2021/08/21 14:00 | Albion v Annan Athletic | W | 0-1 |
| Skottland - League Two | 2021/08/14 14:00 | Annan Athletic v Stirling | W | 3-1 |
| Skottland - League Challenge Cup | 2021/08/11 18:45 | Celtic B v Annan Athletic | L | 2-0 |
| Skottland - League Two | 2021/08/07 14:00 | Stranraer v Annan Athletic | W | 0-3 |
| Skottland - League Two | 2021/07/31 14:00 | Annan Athletic v Forfar | L | 0-2 |
| Skottland - League Cup | 2021/07/24 14:00 | Motherwell v Annan Athletic | L | 2-0 |
| Skottland - League Cup | 2021/07/20 18:45 | Annan Athletic v Queen's Park | L | 1-2 |
Away History
| Skottland - League Challenge Cup | 2021/09/04 14:00 | Cove Rangers v Stenhousemuir | L | 4-2 |
| Skottland - League Two | 2021/08/28 14:00 | Stenhousemuir v Kelty Hearts | L | 1-4 |
| Skottland - League Two | 2021/08/21 14:00 | Stenhousemuir v Cowdenbeath | D | 1-1 |
| Skottland - League Two | 2021/08/13 18:45 | FC Edinburgh v Stenhousemuir | L | 1-0 |
| Skottland - League Challenge Cup | 2021/08/10 18:30 | Stenhousemuir v Dundee Utd B | W | 3-0 |
| Skottland - League Two | 2021/08/07 14:00 | Albion v Stenhousemuir | D | 2-2 |
| Skottland - League Two | 2021/07/31 14:00 | Stenhousemuir v Stirling | L | 0-1 |
| Skottland - League Cup | 2021/07/24 14:00 | Dunfermline v Stenhousemuir | L | 4-1 |