| 1. Round | 02/08/2019 | Dunfermline Athletic | - | Dundee FC | 2:2 |  |
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| 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 | ||||
| 5. Round | 14/09/2019 | Dunfermline Athletic | - | Inverness CT | 0:1 | ||||
| 7. Round | 28/09/2019 | Dunfermline Athletic | - | Alloa Athletic | 1:1 | ||||
| 9. Round | 19/10/2019 | Dunfermline Athletic | - | Ayr United | 3:2 |
England