5. Round | 14/09/2019 | Ayr United | - | Dundee United | 2:0 | ||||
7. Round | 28/09/2019 | Dundee United | - | Greenock Morton FC | 6:0 | ||||
8. Round | 04/10/2019 | Alloa Athletic | - | Dundee United | 1:0 | ||||
9. Round | 19/10/2019 | Queen Of The South | - | Dundee United | 4:0 | ||||
10. Round | 26/10/2019 | Dundee United | - | Dunfermline Athletic | 2:0 |