Head to Head
| Club Friendly List | 2019/07/09 18:45 | Raith v Cowdenbeath | L | 2-1 |
| Scotland League Cup | 2018/07/14 14:00 | Raith v Cowdenbeath | W | 0-2 |
| Scotland League Cup | 2017/07/29 14:00 | Raith v Cowdenbeath | L | 2-0 |
| Scotland League Challenge Cup | 2015/07/25 14:00 | Cowdenbeath v Raith | L | 0-1 |
| Scotland Championship | 2015/04/08 18:45 | Raith v Cowdenbeath | W | 1-3 |
| Scotland Championship | 2015/01/03 15:00 | Cowdenbeath v Raith | L | 0-1 |
| Scotland Championship | 2014/11/15 15:00 | Raith v Cowdenbeath | L | 2-1 |
| Scotland Championship | 2014/08/30 14:00 | Cowdenbeath v Raith | L | 1-3 |
Home History
| Scotland League Two | 2020/11/07 15:00 | Stranraer v Cowdenbeath | L | 2-0 |
| Scotland League Two | 2020/10/31 15:00 | Cowdenbeath v Stenhousemuir | D | 1-1 |
| Scotland League Two | 2020/10/24 14:00 | FC Edinburgh v Cowdenbeath | W | 0-1 |
| Scotland League Two | 2020/10/17 14:00 | Cowdenbeath v Annan Athletic | L | 0-3 |
| Scotland League Cup | 2020/10/13 17:30 | Inverness CT v Cowdenbeath | L | 4-2 |
| Scotland League Cup | 2020/10/10 14:00 | Cowdenbeath v Hearts | L | 0-1 |
| Scotland League Cup | 2020/10/06 18:45 | East Fife v Cowdenbeath | L | 2-0 |
| Scotland League Two | 2020/03/10 19:45 | Elgin v Cowdenbeath | L | 3-2 |
Away History
| Scotland League Cup | 2020/11/10 19:45 | Raith v Inverness CT | W | 6-5 |
| Scotland Championship | 2020/11/07 15:00 | Raith v Morton | W | 5-0 |
| Scotland Championship | 2020/10/31 15:00 | Dundee v Raith | D | 1-1 |
| Scotland Championship | 2020/10/24 14:00 | Queen of South v Raith | W | 2-5 |
| Scotland Championship | 2020/10/17 14:00 | Raith v Arbroath | W | 3-0 |
| Scotland League Cup | 2020/10/13 18:45 | Hearts v Raith | L | 3-1 |
| Scotland League Cup | 2020/10/10 14:00 | Raith v East Fife | W | 2-1 |
| Scotland League One | 2020/03/07 15:00 | Raith v Forfar | W | 2-1 |