1. Round | 03/08/2019 | Dundee United | - | Inverness CT | 4:1 | ||||
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 | ||||
8. Round | 04/10/2019 | Alloa Athletic | - | Dundee United | 1:0 | ||||
10. Round | 26/10/2019 | Dundee United | - | Dunfermline Athletic | 2:0 | ||||
12. Round | 02/11/2019 | Inverness CT | - | Dundee United | 0:3 | ||||
13. Round | 08/11/2019 | Dundee FC | - | Dundee United | 0:2 | ||||
14. Round | 16/11/2019 | Dundee United | - | Queen Of The South | 3:0 | ||||
20. Round | 04/01/2020 | Queen Of The South | - | Dundee United | 0:1 |