Head to Head
| Scotland League Two | 2023/05/06 14:00 | Stenhousemuir v Annan Athletic | W | 2-1 |
| Scotland League Two | 2023/03/04 15:00 | Annan Athletic v Stenhousemuir | W | 2-3 |
| Scotland League Two | 2022/10/08 14:00 | Stenhousemuir v Annan Athletic | D | 2-2 |
| Scotland League Two | 2022/08/06 14:00 | Annan Athletic v Stenhousemuir | L | 2-1 |
| Scotland League Two | 2022/04/02 14:00 | Stenhousemuir v Annan Athletic | L | 0-1 |
| Scotland League Two | 2022/02/05 15:00 | Annan Athletic v Stenhousemuir | W | 0-2 |
| Scotland League Two | 2021/11/13 15:00 | Stenhousemuir v Annan Athletic | W | 2-0 |
| Scotland League Two | 2021/09/11 14:00 | Annan Athletic v Stenhousemuir | W | 1-2 |
| Scotland League Two | 2021/04/27 18:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
| Scotland League Two | 2021/04/20 18:45 | Annan Athletic v Stenhousemuir | L | 5-1 |
| Scotland League Two | 2020/11/21 15:00 | Stenhousemuir v Annan Athletic | L | 1-2 |
| Scotland League Two | 2020/02/01 15:00 | Annan Athletic v Stenhousemuir | W | 0-3 |
| Scotland League Two | 2019/12/07 15:00 | Stenhousemuir v Annan Athletic | L | 1-2 |
| Scotland League Two | 2019/08/31 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
| Scotland League One Play-Offs | 2019/05/11 14:00 | Stenhousemuir v Annan Athletic | L | 1-2 |
| Scotland League One Play-Offs | 2019/05/07 18:45 | Annan Athletic v Stenhousemuir | L | 2-0 |
| Scotland League Two | 2018/04/14 14:00 | Stenhousemuir v Annan Athletic | W | 3-2 |
| Scotland League Two | 2018/02/24 15:00 | Annan Athletic v Stenhousemuir | L | 2-0 |
| Scotland League Two | 2017/12/09 15:00 | Stenhousemuir v Annan Athletic | L | 1-3 |
| Scotland League Two | 2017/09/16 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |