| 3. Round | 24/08/2019 | Ross County FC | - | Livingston FC | 1:4 |  |
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| 4. Round | 31/08/2019 | Livingston FC | - | St. Mirren FC | 2:1 | ||||
| 6. Round | 21/09/2019 | Livingston FC | - | Aberdeen FC | 0:2 | ||||
| 7. Round | 28/09/2019 | Hamilton Academical | - | Livingston FC | 2:1 |
| 3. Round | 24/08/2019 | Ross County FC | - | Livingston FC | 1:4 | |
|||
| 4. Round | 31/08/2019 | Livingston FC | - | St. Mirren FC | 2:1 | ||||
| 6. Round | 21/09/2019 | Livingston FC | - | Aberdeen FC | 0:2 | ||||
| 7. Round | 28/09/2019 | Hamilton Academical | - | Livingston FC | 2:1 |
| Jack Thomas Stobbs | |
| Born: | 27.02.1997 |
| Place of birth: |
Leeds, 
England |
| Nationality: |
England
|
| Height: | 180 cm |
| Weight: | 85 kg |
| Position(s): | Centre Forward Right Winger |
| Foot: | right |