[7] Cowdenbeath 2-4 Annan Athletic [4] 2019-02-16 15:00
Vreme: Frig Stadium: Central Park Gazon: Vreme buna Round: 25
Head to Head
| Scotia - League Two | 2018/11/10 15:00 | Annan Athletic v Cowdenbeath | W | 0-2 |
| Scotia - League Two | 2018/08/11 14:00 | Cowdenbeath v Annan Athletic | L | 1-2 |
| Scotia - League Two | 2018/04/28 14:00 | Cowdenbeath v Annan Athletic | L | 0-2 |
| Scotia - League Two | 2018/02/03 15:00 | Annan Athletic v Cowdenbeath | D | 1-1 |
| Scotia - League Two | 2017/11/18 15:00 | Cowdenbeath v Annan Athletic | D | 1-1 |
| Scotia - League Two | 2017/09/30 14:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
| Scotia - League Two | 2017/03/25 15:00 | Annan Athletic v Cowdenbeath | L | 1-0 |
| Scotia - League Two | 2017/02/18 15:00 | Cowdenbeath v Annan Athletic | L | 0-1 |
| Scotia - League Two | 2016/12/10 15:00 | Annan Athletic v Cowdenbeath | L | 2-0 |
| Scotia - League Two | 2016/10/15 14:00 | Cowdenbeath v Annan Athletic | D | 2-2 |