Head to Head
| Scotland League Two | 2020/02/01 15:00 | Annan Athletic v Stenhousemuir | W | 0-3 |
| Scotland League Two | 2019/12/07 15:00 | Stenhousemuir v Annan Athletic | L | 1-2 |
| Scotland League Two | 2019/08/31 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
| Scotland League One Play-Offs | 2019/05/11 14:00 | Stenhousemuir v Annan Athletic | L | 1-2 |
| Scotland League One Play-Offs | 2019/05/07 18:45 | Annan Athletic v Stenhousemuir | L | 2-0 |
| Scotland League Two | 2018/04/14 14:00 | Stenhousemuir v Annan Athletic | W | 3-2 |
| Scotland League Two | 2018/02/24 15:00 | Annan Athletic v Stenhousemuir | L | 2-0 |
| Scotland League Two | 2017/12/09 15:00 | Stenhousemuir v Annan Athletic | L | 1-3 |
Home History
| Scotland League Cup | 2020/11/14 15:00 | Alloa v Stenhousemuir | L | 4-2 |
| Scotland League Cup | 2020/11/10 19:30 | Stenhousemuir v Livingston | L | 0-4 |
| Scotland League Two | 2020/11/07 15:00 | Stenhousemuir v FC Edinburgh | W | 2-0 |
| Scotland League Two | 2020/10/31 15:00 | Cowdenbeath v Stenhousemuir | D | 1-1 |
| Scotland League Two | 2020/10/24 14:00 | Stenhousemuir v Stirling | D | 2-2 |
| Scotland League Two | 2020/10/17 14:00 | Albion v Stenhousemuir | W | 1-3 |
| Scotland League Cup | 2020/10/13 18:30 | Stenhousemuir v Airdrieonians | L | 0-2 |
| Scotland League Cup | 2020/10/10 14:00 | FC Edinburgh v Stenhousemuir | W | 4-6 |
Away History
| Scotland League Cup | 2020/11/10 19:45 | Albion v Annan Athletic | W | 1-5 |
| Scotland League Two | 2020/11/07 15:00 | Annan Athletic v Albion | L | 2-3 |
| Scotland League Two | 2020/10/31 15:00 | Stirling v Annan Athletic | L | 1-0 |
| Scotland League Two | 2020/10/24 14:00 | Annan Athletic v Stranraer | D | 1-1 |
| Scotland League Two | 2020/10/17 14:00 | Cowdenbeath v Annan Athletic | W | 0-3 |
| Scotland League Cup | 2020/10/13 18:45 | Ayr v Annan Athletic | L | 1-0 |
| Scotland League Cup | 2020/10/10 14:00 | Annan Athletic v Stranraer | L | 5-6 |
| Scotland League Cup | 2020/10/06 18:45 | Annan Athletic v Hamilton | W | 3-1 |