Head to Head
| Scotland League Two | 2021/10/30 14:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2021/08/28 14:00 | Cowdenbeath v Annan Athletic | L | 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 | 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 |
Home History
| Scotland League Two | 2021/12/22 19:45 | Cowdenbeath v FC Edinburgh | L | 1-2 |
| Scotland League Two | 2021/12/18 15:00 | Cowdenbeath v Albion | D | 0-0 |
| Scotland League Two | 2021/12/11 15:00 | Stranraer v Cowdenbeath | L | 2-0 |
| Scotland League Two | 2021/12/04 15:00 | Cowdenbeath v Stirling | W | 1-0 |
| Scotland League Two | 2021/11/20 15:00 | Forfar v Cowdenbeath | L | 3-0 |
| Scotland League Two | 2021/11/13 15:00 | Elgin v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2021/11/06 15:00 | Cowdenbeath v Kelty Hearts | L | 0-1 |
| Scotland League Two | 2021/10/30 14:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
Away History
| Scotland League Two | 2022/01/02 15:00 | Stranraer v Annan Athletic | D | 1-1 |
| Scotland League Two | 2021/12/26 13:00 | Annan Athletic v Kelty Hearts | W | 5-1 |
| Scotland League Two | 2021/12/18 15:00 | Stirling v Annan Athletic | W | 2-3 |
| Scotland League Two | 2021/12/11 15:00 | Annan Athletic v Elgin | W | 4-1 |
| Scotland League Two | 2021/12/03 19:45 | FC Edinburgh v Annan Athletic | W | 0-1 |
| Scotland FA Cup | 2021/11/27 15:00 | Gala Fairydean v Annan Athletic | W | 0-1 |
| Scotland League Two | 2021/11/20 15:00 | Annan Athletic v Albion | D | 1-1 |
| Scotland League Two | 2021/11/13 15:00 | Stenhousemuir v Annan Athletic | L | 2-0 |