Group D | 10/07/2021 | Cowdenbeath FC | - | Raith Rovers | 0:1 | ||||
Group D | 13/07/2021 | Raith Rovers | - | Brechin City FC | 4:0 | ||||
Group D | 21/07/2021 | Livingston FC | - | Raith Rovers | 6:5 pso | ||||
Group D | 24/07/2021 | Raith Rovers | - | Alloa Athletic | 5:4 pso | ||||
Round of 16 | 15/08/2021 | Raith Rovers | - | Aberdeen FC | 2:1 | ||||
Quarter-finals | 23/09/2021 | Celtic FC | - | Raith Rovers | 3:0 |