Head to Head
| Scotland League Two | 2021/08/28 14:00 | Cowdenbeath v Annan Athletic | W | 1-3 |
| 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 | W | 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 | L | 3-1 |
| Scotland League Two | 2019/11/09 15:00 | Annan Athletic v Cowdenbeath | W | 1-0 |
| Scotland League Two | 2019/08/24 14:00 | Cowdenbeath v Annan Athletic | L | 3-1 |
Home History
| Scotland FA Cup | 2021/10/23 14:00 | Annan Athletic v Jeanfield Swifts | W | 3-1 |
| Scotland League Two | 2021/10/16 14:00 | Forfar v Annan Athletic | L | 2-0 |
| Scotland League Two | 2021/10/02 14:00 | Kelty Hearts v Annan Athletic | L | 2-1 |
| Scotland League Two | 2021/09/25 14:00 | Annan Athletic v FC Edinburgh | L | 1-3 |
| Scotland League Two | 2021/09/18 14:00 | Elgin v Annan Athletic | W | 0-2 |
| 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 |
Away History
| Scotland FA Cup | 2021/10/23 14:00 | Cowdenbeath v Civil Service Strollers | L | 2-4 |
| Scotland League Two | 2021/10/16 14:00 | Cowdenbeath v Stenhousemuir | L | 0-2 |
| Scotland League Two | 2021/10/01 18:45 | FC Edinburgh v Cowdenbeath | D | 1-1 |
| Scotland League Two | 2021/09/25 14:00 | Stirling v Cowdenbeath | L | 4-0 |
| Scotland League Two | 2021/09/18 14:00 | Cowdenbeath v Forfar | D | 1-1 |
| Scotland League Two | 2021/09/11 14:00 | Albion v Cowdenbeath | L | 2-1 |
| Scotland League Challenge Cup | 2021/09/04 14:00 | Cowdenbeath v Alloa | L | 0-2 |
| Scotland League Two | 2021/08/31 18:45 | Cowdenbeath v Stranraer | L | 1-2 |