Head to Head
| Scotland League Two | 2021/10/30 14:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2021/08/28 14:00 | Cowdenbeath v Annan Athletic | L | 1-3 |
| Scotland League Two | 2021/05/01 14:00 | Annan Athletic v Cowdenbeath | D | 1-1 |
| 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 | L | 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 | 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 |
| 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 |
| Scotland League Two | 2017/03/25 15:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2017/02/18 15:00 | Cowdenbeath v Annan Athletic | L | 0-1 |
| Scotland League Two | 2016/12/10 15:00 | Annan Athletic v Cowdenbeath | L | 2-0 |
| Scotland League Two | 2016/10/15 14:00 | Cowdenbeath v Annan Athletic | D | 2-2 |