2. Round | 09/08/2019 | Partick Thistle | - | Dundee United | 1:2 | ||||
3. Round | 24/08/2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
4. Round | 30/08/2019 | Dundee United | - | Dundee FC | 6:2 | ||||
5. Round | 14/09/2019 | Ayr United | - | Dundee United | 2:0 | ||||
6. Round | 21/09/2019 | Dundee United | - | Arbroath FC | 2:1 | ||||
7. Round | 28/09/2019 | Dundee United | - | Greenock Morton FC | 6:0 | ||||
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 | ||||
21. Round | 11/01/2020 | Partick Thistle | - | Dundee United | 1:4 | ||||
22. Round | 25/01/2020 | Dundee United | - | Greenock Morton FC | 1:1 | ||||
23. Round | 01/02/2020 | Dundee United | - | Arbroath FC | 0:1 | ||||
24. Round | 14/02/2020 | Alloa Athletic | - | Dundee United | 0:0 | ||||
25. Round | 21/02/2020 | Dundee United | - | Inverness CT | 2:1 | ||||
26. Round | 29/02/2020 | Dunfermline Athletic | - | Dundee United | 2:0 | ||||
27. Round | 03/03/2020 | Ayr United | - | Dundee United | 0:0 | ||||
28. Round | 07/03/2020 | Dundee United | - | Partick Thistle | 1:1 |