Head to Head
| 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 |
Home History
| Scotland League Two | 2021/11/09 19:30 | Stenhousemuir v Albion | W | 3-1 |
| Scotland League Two | 2021/11/06 15:00 | Stirling v Stenhousemuir | W | 1-3 |
| Scotland FA Cup | 2021/10/23 14:00 | Stenhousemuir v Huntly | W | 4-1 |
| Scotland League Two | 2021/10/16 14:00 | Cowdenbeath v Stenhousemuir | W | 0-2 |
| Scotland League Two | 2021/10/02 14:00 | Stenhousemuir v Forfar | D | 1-1 |
| Scotland League Two | 2021/09/25 14:00 | Stenhousemuir v Elgin | L | 1-2 |
| Scotland League Two | 2021/09/18 14:00 | Stranraer v Stenhousemuir | L | 2-0 |
| Scotland League Two | 2021/09/11 14:00 | Annan Athletic v Stenhousemuir | W | 1-2 |
Away History
| Scotland League Two | 2021/11/06 15:00 | Annan Athletic v Stranraer | D | 2-2 |
| Scotland League Two | 2021/10/30 14:00 | Annan Athletic v Cowdenbeath | W | 1-0 |
| Scotland FA Cup | 2021/10/23 14:00 | Annan Athletic v Jeanfield Swifts | W | 3-1 |
| Scotland League Two | 2021/10/16 14:00 | Forfar v Annan Athletic | L | 2-0 |
| Scotland League Two | 2021/10/02 14:00 | Kelty Hearts v Annan Athletic | L | 2-1 |
| Scotland League Two | 2021/09/25 14:00 | Annan Athletic v FC Edinburgh | L | 1-3 |
| Scotland League Two | 2021/09/18 14:00 | Elgin v Annan Athletic | W | 0-2 |
| Scotland League Two | 2021/09/11 14:00 | Annan Athletic v Stenhousemuir | L | 1-2 |