Head to Head
| 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 |
| Skottland - League Two | 2018/04/14 14:00 | Stenhousemuir v Annan Athletic | L | 3-2 |
| Skottland - League Two | 2018/02/24 15:00 | Annan Athletic v Stenhousemuir | W | 2-0 |
| Skottland - League Two | 2017/12/09 15:00 | Stenhousemuir v Annan Athletic | W | 1-3 |
| Skottland - League Two | 2017/09/16 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |