| Dundee v Morton FC 31/12/1938 | View match | |
| Airdrieonians (Old) v Dundee 14/01/1939 | View match | |
| Dundee v St Bernard`s 21/01/1939 | View match | |
| Dundee v Cowdenbeath FC 28/01/1939 | View match | |
| Dundee v Clyde 04/02/1939 | View match | |
| Clyde v Dundee 08/02/1939 | View match | |
| Brechin City FC v Dundee 11/02/1939 | View match | |
| Dundee v Kings Park 18/02/1939 | View match | |
| Dundee v Leith Athletic 25/02/1939 | View match | |
| East Stirlingshire FC v Dundee 04/03/1939 | View match | |
| East Fife FC v Dundee 11/03/1939 | View match | |
| Dundee v Dundee United FC 18/03/1939 | View match |