Head to Head
| Scotland League Cup | 2018/07/14 14:00 | Raith v Cowdenbeath | L | 0-2 |
| Scotland League Cup | 2017/07/29 14:00 | Raith v Cowdenbeath | W | 2-0 |
| Scotland League Challenge Cup | 2015/07/25 14:00 | Cowdenbeath v Raith | W | 0-1 |
| Scotland Championship | 2015/04/08 18:45 | Raith v Cowdenbeath | L | 1-3 |
| Scotland Championship | 2015/01/03 15:00 | Cowdenbeath v Raith | W | 0-1 |
| Scotland Championship | 2014/11/15 15:00 | Raith v Cowdenbeath | W | 2-1 |
| Scotland Championship | 2014/08/30 14:00 | Cowdenbeath v Raith | W | 1-3 |
Home History
| Club Friendly List | 2019/07/06 14:00 | Raith v Spartans | W | 2-0 |
| Club Friendly List | 2019/07/04 18:30 | Raith v Hamilton | W | 3-2 |
| Club Friendly List | 2019/06/29 14:00 | Raith v Stirling | W | 1-0 |
| Scotland Championship Play-Offs | 2019/05/18 15:05 | Queen of South v Raith | D | 0-0 |
| Scotland Championship Play-Offs | 2019/05/15 18:45 | Raith v Queen of South | L | 1-3 |
| Scotland Championship Play-Offs | 2019/05/11 14:00 | Forfar v Raith | D | 1-1 |
| Scotland Championship Play-Offs | 2019/05/07 18:45 | Raith v Forfar | W | 2-1 |
| Scotland League One | 2019/05/04 14:00 | Montrose v Raith | D | 1-1 |
Away History
| Club Friendly List | 2019/07/06 14:00 | Airdrieonians v Cowdenbeath | L | 3-0 |
| Scotland League Two | 2019/05/04 14:00 | Cowdenbeath v Clyde | W | 2-1 |
| Scotland League Two | 2019/04/27 14:00 | Annan Athletic v Cowdenbeath | L | 3-2 |
| 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 |