| ScPS | 16/02/19 | Livingston FC | - | Dundee FC | 1:2 |  |
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| ScPS | 03/04/19 | St. Johnstone FC | - | Dundee FC | 2:0 | ||||
| League Cup | 20/07/19 | Dundee FC | - | Peterhead FC | 4:2 pso | ||||
| Championship | 02/08/19 | Dunfermline Athletic | - | Dundee FC | 2:2 | ||||
| Championship | 01/11/19 | Dundee FC | - | Greenock Morton FC | 2:1 |
England