Group D | 10/07/2021 | Brechin City FC | - | Livingston FC | 0:3 | ||||
Group D | 17/07/2021 | Alloa Athletic | - | Livingston FC | 2:1 | ||||
Group D | 21/07/2021 | Livingston FC | - | Raith Rovers | 6:5 pso | ||||
Group D | 24/07/2021 | Livingston FC | - | Cowdenbeath FC | 3:1 | ||||
Round of 16 | 14/08/2021 | Livingston FC | - | St. Mirren FC | 4:3 pso | ||||
Quarter-finals | 22/09/2021 | Rangers FC | - | Livingston FC | 2:0 |