Home History
| Scotland Lowland League | 2021/07/28 18:45 | Stirling University v Celtic B | W | 1-5 |
| Scotland Lowland League | 2021/07/24 12:00 | Celtic B v East Kilbride | D | 1-1 |
Away History
| Scotland League Two | 2021/08/07 14:00 | Stranraer v Annan Athletic | W | 0-3 |
| 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 |