Head to Head
| 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 |
| Scotland League Two | 2018/11/10 15:00 | Annan Athletic v Cowdenbeath | L | 0-2 |
| Scotland League Two | 2018/08/11 14:00 | Cowdenbeath v Annan Athletic | W | 1-2 |
| Scotland League Two | 2018/04/28 14:00 | Cowdenbeath v Annan Athletic | W | 0-2 |
| Scotland League Two | 2018/02/03 15:00 | Annan Athletic v Cowdenbeath | D | 1-1 |
| Scotland League Two | 2017/11/18 15:00 | Cowdenbeath v Annan Athletic | D | 1-1 |
Home History
| Scotland League Two | 2019/11/02 15:00 | Elgin v Annan Athletic | L | 4-0 |
| Scotland FA Cup | 2019/10/26 14:00 | Brechin v Annan Athletic | W | 0-2 |
| Scotland FA Cup | 2019/10/19 14:00 | Annan Athletic v Brechin | D | 2-2 |
| Scotland League Two | 2019/10/05 14:00 | Queen's Park v Annan Athletic | W | 1-2 |
| Scotland League Two | 2019/09/28 14:00 | Cove Rangers v Annan Athletic | L | 3-0 |
| Scotland League Two | 2019/09/21 14:00 | Annan Athletic v Stirling | D | 0-0 |
| Scotland League Two | 2019/09/14 14:00 | FC Edinburgh v Annan Athletic | L | 4-0 |
| Scotland League Two | 2019/08/31 14:00 | Annan Athletic v Stenhousemuir | D | 1-1 |
Away History
| Scotland League Two | 2019/11/02 15:00 | Cowdenbeath v Cove Rangers | L | 1-3 |
| Scotland League Two | 2019/10/29 19:45 | Stirling v Cowdenbeath | D | 0-0 |
| Scotland FA Cup | 2019/10/26 14:00 | Broxburn Athletic v Cowdenbeath | L | 3-0 |
| Scotland FA Cup | 2019/10/19 14:00 | Cowdenbeath v Broxburn Athletic | D | 1-1 |
| Scotland League Two | 2019/10/05 14:00 | Cowdenbeath v FC Edinburgh | W | 1-0 |
| Scotland League Two | 2019/09/28 14:00 | Cowdenbeath v Albion | W | 1-0 |
| Scotland League Two | 2019/09/21 14:00 | Queen's Park v Cowdenbeath | W | 0-3 |
| Scotland League Two | 2019/09/14 14:00 | Stenhousemuir v Cowdenbeath | W | 0-3 |