| St Johnstone FC v Dumbarton 12/09/1959 | View match | |
| Alloa Athletic FC v Dumbarton 16/09/1959 | View match | |
| Dumbarton v Berwick Rangers FC 19/09/1959 | View match | |
| Dundee United FC v Dumbarton 23/09/1959 | View match | |
| Brechin City FC v Dumbarton 26/09/1959 | View match | |
| Dumbarton v Stenhousemuir FC 03/10/1959 | View match | |
| East Fife FC v Dumbarton 10/10/1959 | View match | |
| Dumbarton v Queen Of The South FC 17/10/1959 | View match | |
| Dumbarton v Forfar Athletic FC 24/10/1959 | View match | |
| North Shields F.C. v Dumbarton 31/10/1959 | View match | |
| Morton FC v Dumbarton 07/11/1959 | View match | |
| Falkirk FC v Dumbarton 14/11/1959 | View match |