| 3. Ronde | 31.10.2020 | Dundee FC | - | Raith Rovers | 1:1 | ||||
| 4. Ronde | 07.11.2020 | Raith Rovers | - | Greenock Morton FC | 5:0 | ||||
| 5. Ronde | 21.11.2020 | Inverness CT | - | Raith Rovers | 2:0 | ||||
| 6. Ronde | 05.12.2020 | Raith Rovers | - | Dunfermline Athletic | 2:2 | ||||
| 7. Ronde | 11.12.2020 | Ayr United | - | Raith Rovers | 0:0 | ||||
| 9. Ronde | 26.12.2020 | Alloa Athletic | - | Raith Rovers | 2:5 |  |
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| 10. Ronde | 29.12.2020 | Raith Rovers | - | Queen Of The South | 0:2 |
Duitsland