Home History
| Scotland League Two | 2021/09/11 14:00 | Annan Athletic v Stenhousemuir | L | 1-2 |
| Scotland League Two | 2021/08/28 14:00 | Cowdenbeath v Annan Athletic | W | 1-3 |
| Scotland League Two | 2021/08/21 14:00 | Albion v Annan Athletic | W | 0-1 |
| Scotland League Two | 2021/08/14 14:00 | Annan Athletic v Stirling | W | 3-1 |
| Scotland League Challenge Cup | 2021/08/11 18:45 | Celtic B v Annan Athletic | L | 2-0 |
| 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 |
Away History
| Scotland FA Cup | 2020/12/26 15:00 | Kelty Hearts v Jeanfield Swifts | L | 2-1 |