3. Round | 24/08/2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
8. Round | 04/10/2019 | Alloa Athletic | - | Dundee United | 1:0 | ||||
10. Round | 26/10/2019 | Dundee United | - | Dunfermline Athletic | 2:0 | ||||
11. Round | 29/10/2019 | Dundee United | - | Partick Thistle | 1:0 | ||||
16. Round | 07/12/2019 | Dundee United | - | Alloa Athletic | 2:1 | ||||
15. Round | 10/12/2019 | Greenock Morton FC | - | Dundee United | 1:2 | ||||
18. Round | 21/12/2019 | Dundee United | - | Ayr United | 4:0 | ||||
20. Round | 04/01/2020 | Queen Of The South | - | Dundee United | 0:1 | ||||
21. Round | 11/01/2020 | Partick Thistle | - | Dundee United | 1:4 |