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 | ||||
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 | ||||
14. Round | 23/11/2019 | Inverness CT | - | Dundee FC | 1:0 | ||||
15. Round | 30/11/2019 | Dundee FC | - | Queen Of The South | 1:2 | ||||
16. Round | 07/12/2019 | Arbroath FC | - | Dundee FC | 1:1 | ||||
18. Round | 21/12/2019 | Partick Thistle | - | Dundee FC | 0:1 | ||||
20. Round | 04/01/2020 | Dundee FC | - | Inverness CT | 0:2 |