2. Round | 24/10/2020 | Queen Of The South | - | Raith Rovers | 2:5 | ||||
3. Round | 31/10/2020 | Dundee FC | - | Raith Rovers | 1:1 | ||||
4. Round | 07/11/2020 | Raith Rovers | - | Greenock Morton FC | 5:0 | ||||
9. Round | 26/12/2020 | Alloa Athletic | - | Raith Rovers | 2:5 | ||||
10. Round | 29/12/2020 | Raith Rovers | - | Queen Of The South | 0:2 | ||||
15. Round | 06/02/2021 | Greenock Morton FC | - | Raith Rovers | 0:1 | ||||
27. Round | 30/04/2021 | Raith Rovers | - | Heart of Midlothian | 0:4 |