1. Round | 02/08/2019 | Dunfermline Athletic | - | Dundee FC | 2:2 | ||||
2. Round | 10/08/2019 | Dundee FC | - | Ayr United | 1:0 | ||||
3. Round | 24/08/2019 | Dundee FC | - | Inverness CT | 0:0 | ||||
4. Round | 30/08/2019 | Dundee United | - | Dundee FC | 6:2 | ||||
5. Round | 14/09/2019 | Dundee FC | - | Alloa Athletic | 2:1 | ||||
6. Round | 21/09/2019 | Greenock Morton FC | - | Dundee FC | 1:0 | ||||
7. Round | 27/09/2019 | Queen Of The South | - | Dundee FC | 1:1 | ||||
8. Round | 05/10/2019 | Dundee FC | - | Arbroath FC | 2:0 | ||||
9. Round | 19/10/2019 | Dundee FC | - | Partick Thistle | 1:3 | ||||
10. Round | 25/10/2019 | Ayr United | - | Dundee FC | 1:2 | ||||
11. Round | 29/10/2019 | Alloa Athletic | - | Dundee FC | 0:3 | ||||
12. Round | 01/11/2019 | Dundee FC | - | Greenock Morton FC | 2:1 | ||||
17. Round | 14/12/2019 | Dundee FC | - | Dunfermline Athletic | 4:3 | ||||
18. Round | 21/12/2019 | Partick Thistle | - | Dundee FC | 0:1 | ||||
19. Round | 27/12/2019 | Dundee United | - | Dundee FC | 1:1 | ||||
20. Round | 04/01/2020 | Dundee FC | - | Inverness CT | 0:2 | ||||
22. Round | 24/01/2020 | Dunfermline Athletic | - | Dundee FC | 2:0 |