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 League Two | 2021/07/31 14:00 | Elgin v Stranraer | D | 1-1 |
| Scotland League Cup | 2021/07/24 14:00 | Kilmarnock v Stranraer | L | 2-1 |
| Scotland League Cup | 2021/07/17 14:00 | Stranraer v East Kilbride | W | 1-0 |
| Scotland League Cup | 2021/07/13 18:30 | Clyde v Stranraer | L | 1-0 |
| Scotland League Cup | 2021/07/10 14:00 | Stranraer v Morton | W | 3-0 |
| Club Friendly List | 2021/06/26 13:00 | Raith v Stranraer | L | 4-1 |
| Scotland League One Play-Offs | 2021/05/11 18:45 | Dumbarton v Stranraer | L | 1-0 |
| Scotland League One Play-Offs | 2021/05/08 14:00 | Stranraer v Dumbarton | D | 0-0 |
Away History
| Scotland League Two | 2021/07/31 14:00 | Annan Athletic v Forfar | L | 0-2 |
| Scotland League Cup | 2021/07/24 14:00 | Motherwell v Annan Athletic | L | 2-0 |
| Scotland League Cup | 2021/07/20 18:45 | Annan Athletic v Queen's Park | L | 1-2 |
| Scotland League Cup | 2021/07/13 18:45 | Annan Athletic v Queen of South | L | 1-3 |
| Scotland League Cup | 2021/07/10 14:00 | Airdrieonians v Annan Athletic | W | 5-6 |
| Scotland League Two | 2021/05/01 14:00 | Annan Athletic v Cowdenbeath | D | 1-1 |
| Scotland League Two | 2021/04/29 18:00 | Brechin v Annan Athletic | W | 0-3 |
| Scotland League Two | 2021/04/27 18:00 | Annan Athletic v Stenhousemuir | D | 1-1 |