| Scotland Development League East | 2017/09/12 18:30 | Raith U20 v Cowdenbeath U20 | L | 3-0 |
| Scotland Development League East | 2017/03/22 19:26 | Cowdenbeath U20 v Raith U20 | L | 0-5 |
| Scotland Development League East | 2017/02/01 20:43 | Cowdenbeath U20 v Raith U20 | L | 1-2 |
| Scotland Development League East | 2016/10/18 18:29 | Raith U20 v Cowdenbeath U20 | L | 7-0 |