| Grupo H | 06.10.2020 | Edinburgh City FC | - | Livingston FC | 1:5 | ||||
| Grupo H | 10.10.2020 | Livingston FC | - | Alloa Athletic | 2:1 |  |
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| Grupo H | 10.11.2020 | Stenhousemuir FC | - | Livingston FC | 0:4 | ||||
| Grupo H | 14.11.2020 | Livingston FC | - | Airdrieonians FC | 4:1 | ||||
| Octavos de final | 28.11.2020 | Livingston FC | - | Ayr United | 4:0 | ||||
| Cuartos de final | 16.12.2020 | Livingston FC | - | Ross County FC | 2:0 | ||||
| Semifinales | 24.01.2021 | Livingston FC | - | St. Mirren FC | 1:0 | ||||
| Final | 28.02.2021 | Livingston FC | - | St. Johnstone FC | 0:1 |
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