| 1. Round | 17/10/2020 | Raith Rovers | - | Arbroath FC | 3:0 | ||||
| 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 | ||||
| 5. Round | 21/11/2020 | Inverness CT | - | Raith Rovers | 2:0 | ||||
| 6. Round | 05/12/2020 | Raith Rovers | - | Dunfermline Athletic | 2:2 | ||||
| 7. Round | 11/12/2020 | Ayr United | - | Raith Rovers | 0:0 | ||||
| 9. Round | 26/12/2020 | Alloa Athletic | - | Raith Rovers | 2:5 |  |
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| 10. Round | 29/12/2020 | Raith Rovers | - | Queen Of The South | 0:2 | ||||
| 14. Round | 23/01/2021 | Heart of Midlothian | - | Raith Rovers | 2:3 | ||||
| 8. Round | 26/01/2021 | Raith Rovers | - | Heart of Midlothian | 0:4 |
Scotland