Head to Head
| 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 |
Home History
| Skottland - League Two | 2019/08/24 14:00 | Cowdenbeath v Annan Athletic | L | 3-1 |
| Skottland - League Two | 2019/08/17 14:00 | Annan Athletic v Albion | W | 3-2 |
| Skottland - League Challenge Cup | 2019/08/13 18:45 | Annan Athletic v Kelty Hearts | L | 6-7 |
| Skottland - League Two | 2019/08/10 14:00 | Annan Athletic v Elgin | D | 1-1 |
| Skottland - League Two | 2019/08/03 14:00 | Brechin v Annan Athletic | W | 0-1 |
| Skottland - Ligacupen | 2019/07/27 14:00 | Motherwell v Annan Athletic | L | 4-0 |
| Skottland - Ligacupen | 2019/07/23 18:45 | Annan Athletic v Morton | L | 0-5 |
| Skottland - Ligacupen | 2019/07/16 18:45 | Queen of South v Annan Athletic | L | 8-7 |
Away History
| Skottland - League Two | 2019/08/24 14:00 | Stenhousemuir v FC Edinburgh | L | 1-3 |
| Skottland - League Two | 2019/08/17 14:00 | Elgin v Stenhousemuir | W | 0-1 |
| Skottland - League Challenge Cup | 2019/08/13 18:30 | Stenhousemuir v FC Edinburgh | W | 2-1 |
| Skottland - League Two | 2019/08/10 14:00 | Queen's Park v Stenhousemuir | D | 1-1 |
| Skottland - League Two | 2019/08/03 14:00 | Stenhousemuir v Albion | L | 2-3 |
| Skottland - Ligacupen | 2019/07/27 14:00 | Stenhousemuir v Cowdenbeath | W | 2-0 |
| Skottland - Ligacupen | 2019/07/24 18:45 | Hearts v Stenhousemuir | L | 2-1 |
| Skottland - Ligacupen | 2019/07/20 14:00 | East Fife v Stenhousemuir | L | 2-0 |