1. Round | 02/08/2019 | Dunfermline Athletic | - | Dundee FC | 2:2 | ||||
2. Round | 10/08/2019 | Queen Of The South | - | Dunfermline Athletic | 1:1 | ||||
3. Round | 24/08/2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
4. Round | 31/08/2019 | Arbroath FC | - | Dunfermline Athletic | 1:0 | ||||
11. Round | 29/10/2019 | Dunfermline Athletic | - | Arbroath FC | 2:0 | ||||
12. Round | 02/11/2019 | Dunfermline Athletic | - | Queen Of The South | 2:0 | ||||
13. Round | 09/11/2019 | Alloa Athletic | - | Dunfermline Athletic | 2:1 | ||||
17. Round | 14/12/2019 | Dundee FC | - | Dunfermline Athletic | 4:3 | ||||
18. Round | 21/12/2019 | Inverness CT | - | Dunfermline Athletic | 2:0 | ||||
19. Round | 28/12/2019 | Dunfermline Athletic | - | Alloa Athletic | 1:3 | ||||
20. Round | 04/01/2020 | Dunfermline Athletic | - | Ayr United | 0:1 | ||||
21. Round | 11/01/2020 | Greenock Morton FC | - | Dunfermline Athletic | 3:2 |