Head to Head
| Scotland League Two | 2021/05/01 14:00 | Annan Athletic v Cowdenbeath | D | 1-1 |
| Scotland League Two | 2021/03/20 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2020/10/17 14:00 | Cowdenbeath v Annan Athletic | L | 0-3 |
| Scotland League Two | 2020/03/07 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2020/01/04 15:00 | Cowdenbeath v Annan Athletic | W | 3-1 |
| Scotland League Two | 2019/11/09 15:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2019/08/24 14:00 | Cowdenbeath v Annan Athletic | W | 3-1 |
| Scotland League Two | 2019/04/27 14:00 | Annan Athletic v Cowdenbeath | L | 3-2 |
Home History
| Scotland League Two | 2021/08/21 14:00 | Stenhousemuir v Cowdenbeath | D | 1-1 |
| Scotland League Challenge Cup | 2021/08/10 18:30 | Fraserburgh v Cowdenbeath | W | 0-1 |
| Scotland League Two | 2021/08/07 14:00 | Cowdenbeath v Elgin | W | 3-1 |
| Scotland League Two | 2021/07/31 14:00 | Kelty Hearts v Cowdenbeath | L | 2-0 |
| Scotland League Cup | 2021/07/24 14:00 | Livingston v Cowdenbeath | L | 3-1 |
| Scotland League Cup | 2021/07/17 14:00 | Cowdenbeath v Brechin | W | 3-2 |
| Scotland League Cup | 2021/07/13 18:45 | Alloa v Cowdenbeath | W | 0-1 |
| Scotland League Cup | 2021/07/10 14:00 | Cowdenbeath v Raith | L | 0-1 |
Away History
| 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 |
| 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 |