| Scotland Development League East | 2016/11/29 19:30 | Raith U20 v Stirling U20 | L | 2-0 |
| Scotland Development League East | 2016/10/11 19:00 | Stirling U20 v Raith U20 | D | 2-2 |
| Scotland Development League East | 2017/03/06 19:45 | Alloa U20 v Stirling U20 | D | 4-4 |
| Scotland Development League East | 2017/02/14 20:00 | Stirling U20 v Cowdenbeath U20 | W | 4-1 |
| Scotland Development League East | 2016/12/13 20:00 | Stirling U20 v Berwick U20 | W | 5-0 |
| Scotland Development League East | 2016/11/29 19:30 | Raith U20 v Stirling U20 | L | 2-0 |
| Scotland Development League East | 2016/11/22 20:00 | Stirling U20 v Alloa U20 | W | 2-0 |
| Scotland Development League East | 2016/11/15 19:30 | Forfar U20 v Stirling U20 | L | 2-1 |
| Scotland Development League East | 2016/10/31 19:45 | Cowdenbeath U20 v Stirling U20 | D | 2-2 |
| Scotland Development League East | 2016/10/17 18:45 | Livingston U20 v Stirling U20 | W | 2-6 |
| Scotland Development League East | 2017/02/20 20:48 | Alloa U20 v Raith U20 | W | 0-1 |
| Scotland Development League East | 2017/02/14 18:50 | Raith U20 v Forfar U20 | W | 1-0 |
| Scotland Development League East | 2017/02/01 20:43 | Cowdenbeath U20 v Raith U20 | W | 1-2 |
| Scotland Development League East | 2017/01/17 19:30 | Forfar U20 v Raith U20 | L | 2-1 |
| Scotland Development League East | 2016/11/29 19:30 | Raith U20 v Stirling U20 | W | 2-0 |
| Scotland Development League East | 2016/11/08 19:30 | Raith U20 v Alloa U20 | W | 6-1 |
| Scotland Development League East | 2016/10/26 18:30 | Raith U20 v Berwick U20 | L | 3-6 |
| Scotland Development League East | 2016/10/18 18:29 | Raith U20 v Cowdenbeath U20 | W | 7-0 |