Head to Head
| Schotland - League Two | 2020/11/21 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Schotland - League Two | 2020/02/01 15:00 | Annan Athletic v Stenhousemuir | L | 0-3 |
| Schotland - League Two | 2019/12/07 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Schotland - League Two | 2019/08/31 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
| Schotland - League One - Play-offs | 2019/05/11 14:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Schotland - League One - Play-offs | 2019/05/07 18:45 | Annan Athletic v Stenhousemuir | W | 2-0 |
| Schotland - League Two | 2018/04/14 14:00 | Stenhousemuir v Annan Athletic | L | 3-2 |
| Schotland - League Two | 2018/02/24 15:00 | Annan Athletic v Stenhousemuir | W | 2-0 |
Home History
| Schotland - League Two | 2021/04/17 11:00 | Annan Athletic v Brechin | W | 3-0 |
| Schotland - League Two | 2021/04/13 18:00 | Queen's Park v Annan Athletic | L | 1-0 |
| Schotland - League Two | 2021/04/10 14:00 | Annan Athletic v Stirling | L | 1-2 |
| Schotland - League Two | 2021/04/06 18:00 | FC Edinburgh v Annan Athletic | D | 1-1 |
| Schotland - League Two | 2021/04/03 14:00 | Annan Athletic v Elgin | L | 0-3 |
| Schotland - League Two | 2021/03/27 15:00 | Albion v Annan Athletic | D | 1-1 |
| Schotland - FA Cup | 2021/03/23 19:45 | Formartine United v Annan Athletic | L | 4-2 |
| Schotland - League Two | 2021/03/20 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
Away History
| Schotland - League Two | 2021/04/15 18:00 | Stranraer v Stenhousemuir | L | 4-0 |
| Schotland - League Two | 2021/04/13 18:00 | Stenhousemuir v Elgin | W | 2-0 |
| Schotland - League Two | 2021/04/10 14:00 | Stenhousemuir v Queen's Park | L | 1-3 |
| Schotland - League Two | 2021/04/08 18:00 | Stenhousemuir v Cowdenbeath | W | 1-0 |
| Schotland - League Two | 2021/04/06 18:00 | Brechin v Stenhousemuir | D | 1-1 |
| Schotland - FA Cup | 2021/04/03 14:00 | Stenhousemuir v Kilmarnock | L | 0-4 |
| Schotland - League Two | 2021/03/30 18:45 | Stirling v Stenhousemuir | L | 1-0 |
| Schotland - League Two | 2021/03/27 15:00 | FC Edinburgh v Stenhousemuir | L | 3-1 |