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 |
| Scotland League Two | 2017/09/16 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |