[10] Cowdenbeath 0-1 Annan Athletic [4] 2016-09-24 23:00
Weather: Rainy Stadium: Central Park Pitch: Uneven and|cutting up Round: 25
Home History
| Scotland League Two | 2016/09/24 14:00 | Arbroath v Cowdenbeath | D | 0-0 |
| Scotland League Two | 2016/09/17 14:00 | Cowdenbeath v Berwick Rangers | L | 0-2 |
| Scotland League Two | 2016/09/10 14:00 | Montrose v Cowdenbeath | W | 1-2 |
| Scotland League Two | 2016/08/27 14:00 | Clyde v Cowdenbeath | L | 5-3 |
| Scotland League Two | 2016/08/20 14:00 | Cowdenbeath v FC Edinburgh | W | 2-0 |
| Scotland League Challenge Cup | 2016/08/16 18:45 | Cowdenbeath v Celtic U20 | L | 1-2 |
| Scotland League Two | 2016/08/13 14:00 | Forfar v Cowdenbeath | L | 4-3 |
| Scotland League Two | 2016/08/06 14:00 | Cowdenbeath v Elgin | L | 0-1 |
Away History
| Scotland League Two | 2016/09/24 14:00 | Annan Athletic v FC Edinburgh | D | 1-1 |
| Scotland League Two | 2016/09/17 14:00 | Arbroath v Annan Athletic | D | 1-1 |
| Scotland League Two | 2016/09/10 14:00 | Annan Athletic v Forfar | L | 1-2 |
| Scotland League Two | 2016/08/27 14:00 | Montrose v Annan Athletic | D | 2-2 |
| Scotland League Two | 2016/08/20 14:00 | Annan Athletic v Clyde | W | 3-2 |
| Scotland League Two | 2016/08/13 14:00 | Berwick Rangers v Annan Athletic | L | 2-0 |
| Scotland League Two | 2016/08/06 14:00 | Annan Athletic v Stirling | W | 3-2 |
| Scotland League Challenge Cup | 2016/08/02 18:45 | Celtic U20 v Annan Athletic | L | 5-1 |