| 1. Round | 06/08/2016 | Ayr United | - | Raith Rovers | 0:2 | ||||
| 2. Round | 13/08/2016 | Raith Rovers | - | St. Mirren FC | 3:1 | ||||
| 3. Round | 20/08/2016 | Raith Rovers | - | Dunfermline Athletic | 2:0 | ||||
| 4. Round | 27/08/2016 | Dundee United | - | Raith Rovers | 2:2 | ||||
| 5. Round | 10/09/2016 | Raith Rovers | - | Falkirk FC | 0:2 | ||||
| 6. Round | 17/09/2016 | Queen Of The South | - | Raith Rovers | 3:1 | ||||
| 9. Round | 15/10/2016 | Raith Rovers | - | Hibernian FC | 0:0 | ||||
| 10. Round | 22/10/2016 | Falkirk FC | - | Raith Rovers | 2:4 | ||||
| 11. Round | 29/10/2016 | Raith Rovers | - | Queen Of The South | 1:0 | ||||
| 14. Round | 19/11/2016 | Dumbarton FC | - | Raith Rovers | 0:0 | ||||
| 16. Round | 10/12/2016 | St. Mirren FC | - | Raith Rovers | 1:0 | ||||
| 17. Round | 17/12/2016 | Raith Rovers | - | Dundee United | 0:0 |
Scotland