[4] Annan Athletic 3-2 Cowdenbeath [7] 2019-04-27 14:00
Weather: Good Stadium: Galabank Pitch: Artificial Turf Round: 35
Head to Head
| 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 |
| Scotland League Two | 2018/08/11 14:00 | Cowdenbeath v Annan Athletic | W | 1-2 |
| Scotland League Two | 2018/04/28 14:00 | Cowdenbeath v Annan Athletic | W | 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 | W | 1-0 |
| Scotland League Two | 2017/03/25 15:00 | Annan Athletic v Cowdenbeath | W | 1-0 |
Home History
| Scotland League Two | 2019/04/20 14:00 | Queen's Park v Annan Athletic | W | 0-3 |
| Scotland League Two | 2019/04/13 14:00 | Annan Athletic v Stirling | D | 2-2 |
| Scotland League Two | 2019/04/06 14:00 | Annan Athletic v Berwick Rangers | W | 6-0 |
| Scotland League Two | 2019/03/30 15:00 | Elgin v Annan Athletic | W | 0-1 |
| Scotland League Two | 2019/03/23 15:00 | Clyde v Annan Athletic | L | 2-1 |
| Scotland League Two | 2019/03/16 15:00 | Annan Athletic v FC Edinburgh | W | 3-1 |
| Scotland League Two | 2019/03/09 15:00 | Peterhead v Annan Athletic | L | 2-1 |
| Scotland League Two | 2019/03/02 15:00 | Annan Athletic v Queen's Park | W | 2-1 |
Away History
| Scotland League Two | 2019/04/20 14:00 | Stirling v Cowdenbeath | W | 0-1 |
| Scotland League Two | 2019/04/13 14:00 | Cowdenbeath v Elgin | W | 2-1 |
| Scotland League Two | 2019/04/06 14:00 | Cowdenbeath v FC Edinburgh | W | 4-1 |
| Scotland League Two | 2019/03/30 15:00 | Peterhead v Cowdenbeath | L | 2-1 |
| Scotland League Two | 2019/03/26 19:45 | Albion v Cowdenbeath | L | 1-0 |
| Scotland League Two | 2019/03/23 15:00 | Cowdenbeath v Queen's Park | D | 0-0 |
| Scotland League Two | 2019/03/09 15:00 | Berwick Rangers v Cowdenbeath | D | 1-1 |
| Scotland League Two | 2019/03/05 19:45 | Cowdenbeath v Peterhead | L | 1-3 |