Head to Head
| 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 |
| Scotland League Two | 2019/02/16 15:00 | Cowdenbeath v Annan Athletic | L | 2-4 |
| Scotland League Two | 2018/11/10 15:00 | Annan Athletic v Cowdenbeath | W | 0-2 |
| Scotland League Two | 2018/08/11 14:00 | Cowdenbeath v Annan Athletic | L | 1-2 |
| Scotland League Two | 2018/04/28 14:00 | Cowdenbeath v Annan Athletic | L | 0-2 |
| Scotland League Two | 2018/02/03 15:00 | Annan Athletic v Cowdenbeath | D | 1-1 |
Home History
| Scotland League Two | 2019/12/28 15:00 | FC Edinburgh v Cowdenbeath | L | 2-0 |
| Scotland League Two | 2019/12/21 15:00 | Cowdenbeath v Stenhousemuir | W | 3-1 |
| Scotland League Two | 2019/12/14 15:00 | Brechin v Cowdenbeath | L | 2-1 |
| Scotland League Two | 2019/12/07 15:00 | Cowdenbeath v Elgin | D | 0-0 |
| Scotland League Two | 2019/11/16 15:00 | Cowdenbeath v Queen's Park | W | 1-0 |
| Scotland League Two | 2019/11/09 15:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
| 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 |
Away History
| Scotland League Two | 2019/12/28 15:00 | Annan Athletic v Queen's Park | W | 3-2 |
| Scotland League Two | 2019/12/21 15:00 | Albion v Annan Athletic | L | 4-2 |
| Scotland League Two | 2019/12/14 15:00 | Annan Athletic v FC Edinburgh | L | 0-2 |
| Scotland League Two | 2019/12/07 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Scotland League Two | 2019/11/30 15:00 | Annan Athletic v Cove Rangers | W | 6-1 |
| Scotland FA Cup | 2019/11/23 15:00 | FC Edinburgh v Annan Athletic | L | 4-3 |
| Scotland League Two | 2019/11/16 15:00 | Stirling v Annan Athletic | L | 2-0 |
| Scotland League Two | 2019/11/12 19:45 | Annan Athletic v Brechin | W | 5-2 |