| 20. Round | 04/01/2020 | Dunfermline Athletic | - | Ayr United | 0:1 | ||||
| 21. Round | 11/01/2020 | Greenock Morton FC | - | Dunfermline Athletic | 3:2 | ||||
| 22. Round | 24/01/2020 | Dunfermline Athletic | - | Dundee FC | 2:0 | ||||
| 24. Round | 25/02/2020 | Dunfermline Athletic | - | Inverness CT | 1:2 | ||||
| 26. Round | 29/02/2020 | Dunfermline Athletic | - | Dundee United | 2:0 | ||||
| 27. Round | 04/03/2020 | Arbroath FC | - | Dunfermline Athletic | 0:0 | ||||
| 28. Round | 07/03/2020 | Dunfermline Athletic | - | Queen Of The South | 1:1 | ||||
| 25. Round | 10/03/2020 | Partick Thistle | - | Dunfermline Athletic | 1:1 |
Scotland