Head to Head
| Scotland League Two | 2020/10/17 14:00 | Cowdenbeath v Annan Athletic | W | 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 | L | 3-1 |
| Scotland League Two | 2019/11/09 15:00 | Annan Athletic v Cowdenbeath | W | 1-0 |
| Scotland League Two | 2019/08/24 14:00 | Cowdenbeath v Annan Athletic | L | 3-1 |
| Scotland League Two | 2019/04/27 14:00 | Annan Athletic v Cowdenbeath | W | 3-2 |
| Scotland League Two | 2019/02/16 15:00 | Cowdenbeath v Annan Athletic | W | 2-4 |
| Scotland League Two | 2018/11/10 15:00 | Annan Athletic v Cowdenbeath | L | 0-2 |
Home History
| Scotland League Two | 2021/01/02 15:00 | Stranraer v Annan Athletic | L | 2-0 |
| Scotland FA Cup | 2020/12/26 15:00 | Gala Fairydean v Annan Athletic | W | 1-2 |
| Scotland League Two | 2020/12/22 19:45 | Brechin v Annan Athletic | D | 0-0 |
| Scotland League Two | 2020/12/19 15:00 | Annan Athletic v Queen's Park | L | 1-2 |
| Scotland League Two | 2020/12/05 15:00 | Elgin v Annan Athletic | L | 1-0 |
| Scotland League Two | 2020/11/28 15:00 | Annan Athletic v FC Edinburgh | L | 0-4 |
| Scotland League Two | 2020/11/21 15:00 | Stenhousemuir v Annan Athletic | W | 1-2 |
| Scotland League Cup | 2020/11/10 19:45 | Albion v Annan Athletic | W | 1-5 |
Away History
| Scotland FA Cup | 2020/12/26 15:00 | Cowdenbeath v Wick Academy | W | 2-0 |
| Scotland League Two | 2020/12/19 15:00 | Cowdenbeath v Brechin | W | 2-0 |
| Scotland League Two | 2020/12/12 15:00 | Stirling v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2020/12/05 15:00 | Cowdenbeath v Queen's Park | L | 0-3 |
| Scotland League Two | 2020/11/28 15:00 | Elgin v Cowdenbeath | L | 5-2 |
| Scotland League Cup | 2020/11/14 15:00 | Cowdenbeath v Raith | L | 0-1 |
| Scotland League Two | 2020/11/07 15:00 | Stranraer v Cowdenbeath | L | 2-0 |
| Scotland League Two | 2020/10/31 15:00 | Cowdenbeath v Stenhousemuir | D | 1-1 |