Head to Head
| 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 |
| 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 |
Home History
| Scotland League Cup | 2020/10/13 17:30 | Inverness CT v Cowdenbeath | L | 4-2 |
| Scotland League Cup | 2020/10/10 14:00 | Cowdenbeath v Hearts | L | 0-1 |
| Scotland League Cup | 2020/10/06 18:45 | East Fife v Cowdenbeath | L | 2-0 |
| Scotland League Two | 2020/03/10 19:45 | Elgin v Cowdenbeath | L | 3-2 |
| Scotland League Two | 2020/03/07 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2020/03/03 19:45 | Cowdenbeath v Albion | W | 2-1 |
| Scotland League Two | 2020/02/29 15:00 | Cowdenbeath v FC Edinburgh | D | 1-1 |
| Scotland League Two | 2020/02/15 15:00 | Cowdenbeath v Stirling | L | 1-4 |
Away History
| Scotland League Cup | 2020/10/13 18:45 | Ayr v Annan Athletic | L | 1-0 |
| Scotland League Cup | 2020/10/10 14:00 | Annan Athletic v Stranraer | L | 5-6 |
| Scotland League Cup | 2020/10/06 18:45 | Annan Athletic v Hamilton | W | 3-1 |
| Scotland League Two | 2020/03/07 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2020/02/29 15:00 | Queen's Park v Annan Athletic | L | 2-0 |
| Scotland League Two | 2020/02/22 15:00 | Annan Athletic v Albion | W | 2-1 |
| Scotland League Two | 2020/02/08 15:00 | FC Edinburgh v Annan Athletic | L | 3-0 |
| Scotland League Two | 2020/02/01 15:00 | Annan Athletic v Stenhousemuir | L | 0-3 |