| Blairgowrie Amaateurs v Dumbarton 21/01/1939 | View match | |
| Dumbarton v East Fife FC 28/01/1939 | View match | |
| Dumbarton v Brechin City FC 04/02/1939 | View match | |
| Airdrieonians (Old) v Dumbarton 11/02/1939 | View match | |
| East Stirlingshire FC v Dumbarton 18/02/1939 | View match | |
| Dumbarton v Dunfermline Athletic 25/02/1939 | View match | |
| Stenhousemuir FC v Dumbarton 04/03/1939 | View match | |
| Morton FC v Dumbarton 18/03/1939 | View match | |
| Dumbarton v St Bernard`s 01/04/1939 | View match | |
| Alloa Athletic FC v Dumbarton 08/04/1939 | View match | |
| Dundee v Dumbarton 15/04/1939 | View match | |
| Dumbarton v Edinburgh City 22/04/1939 | View match |