[7] Cowdenbeath 2-4 Annan Athletic [4] 2019-02-16 15:00
Weather: Cold Stadium: Central Park Pitch: Good Round: 25
Head to Head
| 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 |
Home History
| Scotland League Two | 2019/02/09 15:00 | Queen's Park v Cowdenbeath | D | 1-1 |
| Scotland FA Cup | 2019/01/30 19:45 | Cowdenbeath v Rangers | L | 1-3 |
| Scotland League Two | 2019/01/26 15:00 | Clyde v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2019/01/12 15:00 | Elgin v Cowdenbeath | W | 1-4 |
| Scotland League Two | 2019/01/05 15:00 | Cowdenbeath v Berwick Rangers | W | 2-0 |
| Scotland League Two | 2018/12/29 15:00 | Stirling v Cowdenbeath | L | 2-1 |
| Scotland League Two | 2018/12/22 15:00 | Cowdenbeath v FC Edinburgh | L | 0-2 |
| Scotland League Two | 2018/12/08 15:00 | Cowdenbeath v Clyde | D | 1-1 |
Away History
| Scotland League Two | 2019/02/09 15:00 | Annan Athletic v Clyde | D | 1-1 |
| Scotland League Two | 2019/01/26 15:00 | Annan Athletic v Peterhead | W | 3-0 |
| Scotland League Two | 2019/01/19 15:00 | FC Edinburgh v Annan Athletic | W | 1-2 |
| Scotland League Two | 2019/01/12 15:00 | Stirling v Annan Athletic | L | 2-1 |
| Scotland League Two | 2019/01/05 15:00 | Annan Athletic v Elgin | W | 2-0 |
| Scotland League Two | 2018/12/29 15:00 | Albion v Annan Athletic | D | 1-1 |
| Scotland League Two | 2018/12/22 15:00 | Annan Athletic v Berwick Rangers | W | 4-0 |
| Scotland League Two | 2018/12/15 15:00 | Clyde v Annan Athletic | L | 1-0 |