Head to Head
| 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 | L | 1-2 |
| Schotland - League One - Play-offs | 2019/05/07 18:45 | Annan Athletic v Stenhousemuir | L | 2-0 |
| Schotland - League Two | 2018/04/14 14:00 | Stenhousemuir v Annan Athletic | W | 3-2 |
| Schotland - League Two | 2018/02/24 15:00 | Annan Athletic v Stenhousemuir | L | 2-0 |
| Schotland - League Two | 2017/12/09 15:00 | Stenhousemuir v Annan Athletic | L | 1-3 |
| Schotland - League Two | 2017/09/16 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
Home History
| Schotland - League Two | 2019/12/03 19:45 | Stenhousemuir v Elgin | D | 2-2 |
| Schotland - League Two | 2019/11/30 15:00 | Brechin v Stenhousemuir | W | 1-2 |
| Schotland - League Challenge Cup | 2019/11/16 15:00 | Stenhousemuir v Partick | L | 1-4 |
| Schotland - League Two | 2019/11/09 15:00 | Albion v Stenhousemuir | L | 2-1 |
| Schotland - League Two | 2019/11/02 15:00 | Stenhousemuir v Queen's Park | L | 0-3 |
| Schotland - League Two | 2019/10/29 19:45 | FC Edinburgh v Stenhousemuir | L | 4-0 |
| Schotland - FA Cup | 2019/10/26 13:30 | Penicuik Ath v Stenhousemuir | L | 3-0 |
| Schotland - League Challenge Cup | 2019/10/11 18:35 | Stenhousemuir v Waterford FC | W | 3-2 |
Away History
| Schotland - League Two | 2019/11/30 15:00 | Annan Athletic v Cove Rangers | W | 6-1 |
| Schotland - FA Cup | 2019/11/23 15:00 | FC Edinburgh v Annan Athletic | L | 4-3 |
| Schotland - League Two | 2019/11/16 15:00 | Stirling v Annan Athletic | L | 2-0 |
| Schotland - League Two | 2019/11/12 19:45 | Annan Athletic v Brechin | W | 5-2 |
| Schotland - League Two | 2019/11/09 15:00 | Annan Athletic v Cowdenbeath | W | 1-0 |
| Schotland - League Two | 2019/11/02 15:00 | Elgin v Annan Athletic | L | 4-0 |
| Schotland - FA Cup | 2019/10/26 14:00 | Brechin v Annan Athletic | W | 0-2 |
| Schotland - FA Cup | 2019/10/19 14:00 | Annan Athletic v Brechin | D | 2-2 |