Head to Head
| Schotland - League Two | 2022/01/08 15:00 | Cowdenbeath v Annan Athletic | W | 1-3 |
| Schotland - League Two | 2021/10/30 14:00 | Annan Athletic v Cowdenbeath | W | 1-0 |
| Schotland - League Two | 2021/08/28 14:00 | Cowdenbeath v Annan Athletic | W | 1-3 |
| Schotland - League Two | 2021/05/01 14:00 | Annan Athletic v Cowdenbeath | D | 1-1 |
| Schotland - League Two | 2021/03/20 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
| Schotland - League Two | 2020/10/17 14:00 | Cowdenbeath v Annan Athletic | W | 0-3 |
| Schotland - League Two | 2020/03/07 15:00 | Annan Athletic v Cowdenbeath | D | 0-0 |
| Schotland - League Two | 2020/01/04 15:00 | Cowdenbeath v Annan Athletic | L | 3-1 |
Home History
| Schotland - League Two | 2022/04/02 14:00 | Stenhousemuir v Annan Athletic | W | 0-1 |
| Schotland - League Two | 2022/03/26 15:00 | Annan Athletic v Albion | L | 2-4 |
| Schotland - League Two | 2022/03/19 15:00 | Stirling v Annan Athletic | W | 0-3 |
| Schotland - League Two | 2022/03/12 15:00 | Annan Athletic v Elgin | W | 2-1 |
| Schotland - League Two | 2022/03/05 15:00 | Annan Athletic v Stranraer | W | 4-1 |
| Schotland - League Two | 2022/03/02 19:45 | Albion v Annan Athletic | W | 1-4 |
| Schotland - League Two | 2022/02/26 15:00 | Kelty Hearts v Annan Athletic | L | 3-1 |
| Schotland - League Two | 2022/02/19 15:00 | Annan Athletic v FC Edinburgh | W | 2-1 |
Away History
| Schotland - League Two | 2022/04/02 14:00 | Cowdenbeath v Stirling | D | 0-0 |
| Schotland - League Two | 2022/03/26 15:00 | Forfar v Cowdenbeath | D | 1-1 |
| Schotland - League Two | 2022/03/19 15:00 | Cowdenbeath v Stenhousemuir | D | 1-1 |
| Schotland - League Two | 2022/03/15 19:45 | Cowdenbeath v Forfar | L | 1-2 |
| Schotland - League Two | 2022/03/12 15:00 | Stranraer v Cowdenbeath | L | 3-0 |
| Schotland - League Two | 2022/03/08 19:45 | Stirling v Cowdenbeath | L | 2-1 |
| Schotland - League Two | 2022/03/05 15:00 | Cowdenbeath v Kelty Hearts | L | 0-1 |
| Schotland - League Two | 2022/02/25 19:45 | FC Edinburgh v Cowdenbeath | L | 1-0 |