Head to Head
| 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 |
| Scotland League Two | 2019/04/27 14:00 | Annan Athletic v Cowdenbeath | W | 3-2 |
| Scotland League Two | 2019/02/16 15:00 | Cowdenbeath v Annan Athletic | W | 2-4 |
Home History
| Scotland League Two | 2021/04/29 18:00 | Brechin v Annan Athletic | W | 0-3 |
| Scotland League Two | 2021/04/27 18:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
| Scotland League Two | 2021/04/24 14:00 | Albion v Annan Athletic | L | 1-0 |
| Scotland League Two | 2021/04/20 18:45 | Annan Athletic v Stenhousemuir | W | 5-1 |
| Scotland League Two | 2021/04/17 11:00 | Annan Athletic v Brechin | W | 3-0 |
| Scotland League Two | 2021/04/13 18:00 | Queen's Park v Annan Athletic | L | 1-0 |
| Scotland League Two | 2021/04/10 14:00 | Annan Athletic v Stirling | L | 1-2 |
| Scotland League Two | 2021/04/06 18:00 | FC Edinburgh v Annan Athletic | D | 1-1 |
Away History
| Scotland League Two | 2021/04/27 18:00 | Cowdenbeath v Brechin | L | 0-2 |
| Scotland League Two | 2021/04/24 14:00 | Stenhousemuir v Cowdenbeath | W | 0-2 |
| Scotland League Two | 2021/04/20 18:45 | Brechin v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2021/04/17 11:00 | Cowdenbeath v Stirling | L | 1-5 |
| Scotland League Two | 2021/04/13 18:00 | Albion v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2021/04/10 14:00 | Cowdenbeath v Elgin | W | 1-0 |
| Scotland League Two | 2021/04/08 18:00 | Stenhousemuir v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2021/04/06 18:00 | Queen's Park v Cowdenbeath | L | 3-0 |