Head to Head
| Scotland League Two | 2021/01/02 15:00 | Stranraer v Annan Athletic | W | 2-0 |
| Scotland League Two | 2020/10/24 14:00 | Annan Athletic v Stranraer | D | 1-1 |
| Scotland League Cup | 2020/10/10 14:00 | Annan Athletic v Stranraer | W | 5-6 |
| Club Friendly List | 2019/06/27 18:30 | Annan Athletic v Stranraer | L | 1-0 |
| Club Friendly List | 2018/06/26 18:30 | Annan Athletic v Stranraer | W | 2-4 |
| Scotland League Cup | 2016/07/16 14:00 | Annan Athletic v Stranraer | W | 1-2 |
Home History
| Scotland FA Cup | 2021/01/09 18:00 | Kelty Hearts v Stranraer | W | 2-3 |
| Scotland League Two | 2021/01/02 15:00 | Stranraer v Annan Athletic | W | 2-0 |
| Scotland FA Cup | 2020/12/26 15:00 | Stranraer v Spartans | W | 5-0 |
| Scotland League Two | 2020/12/19 15:00 | Stranraer v Albion | W | 4-0 |
| Scotland League Two | 2020/12/12 15:00 | Stenhousemuir v Stranraer | D | 2-2 |
| Scotland League Two | 2020/12/05 15:00 | Stranraer v Stirling | D | 2-2 |
| Scotland League Two | 2020/11/28 15:00 | Brechin v Stranraer | W | 1-4 |
| Scotland League Two | 2020/11/21 15:00 | FC Edinburgh v Stranraer | W | 0-1 |
Away History
| Scotland League Two | 2021/01/02 15:00 | Stranraer v Annan Athletic | L | 2-0 |
| Scotland FA Cup | 2020/12/26 15:00 | Gala Fairydean v Annan Athletic | W | 1-2 |
| Scotland League Two | 2020/12/22 19:45 | Brechin v Annan Athletic | D | 0-0 |
| Scotland League Two | 2020/12/19 15:00 | Annan Athletic v Queen's Park | L | 1-2 |
| Scotland League Two | 2020/12/05 15:00 | Elgin v Annan Athletic | L | 1-0 |
| Scotland League Two | 2020/11/28 15:00 | Annan Athletic v FC Edinburgh | L | 0-4 |
| Scotland League Two | 2020/11/21 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Scotland League Cup | 2020/11/10 19:45 | Albion v Annan Athletic | W | 1-5 |