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 |
Home History
| Skottland - League Two | 2020/01/25 15:00 | Cove Rangers v Annan Athletic | L | 2-0 |
| Skottland - League Two | 2020/01/18 15:00 | Annan Athletic v Stirling | L | 2-3 |
| Skottland - League Two | 2020/01/11 15:00 | Annan Athletic v Elgin | L | 0-4 |
| Skottland - League Two | 2020/01/04 15:00 | Cowdenbeath v Annan Athletic | L | 3-1 |
| Skottland - League Two | 2019/12/28 15:00 | Annan Athletic v Queen's Park | W | 3-2 |
| Skottland - League Two | 2019/12/21 15:00 | Albion v Annan Athletic | L | 4-2 |
| Skottland - League Two | 2019/12/14 15:00 | Annan Athletic v FC Edinburgh | L | 0-2 |
| Skottland - League Two | 2019/12/07 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
Away History
| Skottland - League Two | 2020/01/25 15:00 | Stenhousemuir v FC Edinburgh | L | 1-2 |
| Skottland - League Two | 2020/01/18 15:00 | Elgin v Stenhousemuir | W | 2-3 |
| Skottland - League Two | 2020/01/11 15:00 | Stenhousemuir v Brechin | D | 2-2 |
| Skottland - League Two | 2020/01/04 15:00 | Queen's Park v Stenhousemuir | L | 2-1 |
| Skottland - League Two | 2019/12/28 15:00 | Stenhousemuir v Stirling | L | 0-2 |
| Skottland - League Two | 2019/12/21 15:00 | Cowdenbeath v Stenhousemuir | L | 3-1 |
| Skottland - League Two | 2019/12/14 15:00 | Cove Rangers v Stenhousemuir | L | 2-1 |
| Skottland - League Two | 2019/12/07 15:00 | Stenhousemuir v Annan Athletic | L | 1-2 |