1. Round | 31/07/2021 | Raith Rovers | - | Hamilton Academical | 4:4 | ||||
2. Round | 07/08/2021 | Inverness CT | - | Raith Rovers | 1:0 | ||||
4. Round | 07/09/2021 | Ayr United | - | Raith Rovers | 0:2 | ||||
6. Round | 18/09/2021 | Greenock Morton FC | - | Raith Rovers | 0:1 | ||||
7. Round | 26/09/2021 | Raith Rovers | - | Partick Thistle | 3:2 | ||||
8. Round | 02/10/2021 | Kilmarnock FC | - | Raith Rovers | 1:3 | ||||
11. Round | 26/10/2021 | Dunfermline Athletic | - | Raith Rovers | 1:1 | ||||
12. Round | 30/10/2021 | Raith Rovers | - | Ayr United | 2:1 | ||||
17. Round | 11/12/2021 | Raith Rovers | - | Kilmarnock FC | 1:0 |