| Group H | 10/10/2020 | Livingston FC | - | Alloa Athletic | 2:1 | ||||
| Group H | 14/11/2020 | Livingston FC | - | Airdrieonians FC | 4:1 | ||||
| Round of 16 | 28/11/2020 | Livingston FC | - | Ayr United | 4:0 | ||||
| Quarter-finals | 16/12/2020 | Livingston FC | - | Ross County FC | 2:0 | ||||
| Semi-finals | 24/01/2021 | Livingston FC | - | St. Mirren FC | 1:0 | ||||
| Final | 28/02/2021 | Livingston FC | - | St. Johnstone FC | 0:1 |  |
England
Jamaica