Head to Head
| 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 |
| Scotland League Two | 2017/11/18 15:00 | Cowdenbeath v Annan Athletic | D | 1-1 |
| Scotland League Two | 2017/09/30 14:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
Home History
| Scotland League Two | 2019/08/17 14:00 | Cove Rangers v Cowdenbeath | L | 3-2 |
| Scotland League Challenge Cup | 2019/08/13 18:45 | Hearts U21 v Cowdenbeath | L | 3-1 |
| Scotland League Two | 2019/08/10 14:00 | Cowdenbeath v Stirling | W | 1-0 |
| Scotland League Two | 2019/08/03 14:00 | Elgin v Cowdenbeath | L | 3-0 |
| Scotland League Cup | 2019/07/27 14:00 | Stenhousemuir v Cowdenbeath | L | 2-0 |
| Scotland League Cup | 2019/07/19 18:45 | Dundee Utd v Cowdenbeath | L | 3-0 |
| Scotland League Cup | 2019/07/16 18:45 | Cowdenbeath v Hearts | L | 0-2 |
| Scotland League Cup | 2019/07/13 14:00 | Cowdenbeath v East Fife | W | 2-0 |
Away History
| Scotland League Two | 2019/08/17 14:00 | Annan Athletic v Albion | W | 3-2 |
| Scotland League Challenge Cup | 2019/08/13 18:45 | Annan Athletic v Kelty Hearts | L | 6-7 |
| Scotland League Two | 2019/08/10 14:00 | Annan Athletic v Elgin | D | 1-1 |
| Scotland League Two | 2019/08/03 14:00 | Brechin v Annan Athletic | W | 0-1 |
| Scotland League Cup | 2019/07/27 14:00 | Motherwell v Annan Athletic | L | 4-0 |
| Scotland League Cup | 2019/07/23 18:45 | Annan Athletic v Morton | L | 0-5 |
| Scotland League Cup | 2019/07/16 18:45 | Queen of South v Annan Athletic | L | 8-7 |
| Scotland League Cup | 2019/07/13 14:00 | Annan Athletic v Dumbarton | L | 0-1 |