| Raith Rovers FC v Dumbarton 14/09/1966 | View match | |
| Dumbarton v East Fife FC 17/09/1966 | View match | |
| Dumbarton v Forfar Athletic FC 21/09/1966 | View match | |
| Brechin City FC v Dumbarton 24/09/1966 | View match | |
| Dumbarton v Cowdenbeath FC 01/10/1966 | View match | |
| Hamilton Academicals v Dumbarton 08/10/1966 | View match | |
| Dumbarton v East Stirlingshire FC 15/10/1966 | View match | |
| Stranraer v Dumbarton 22/10/1966 | View match | |
| Dumbarton v Queen Of The South FC 29/10/1966 | View match | |
| Stenhousemuir FC v Dumbarton 05/11/1966 | View match | |
| Dumbarton v Arbroath FC 12/11/1966 | View match | |
| Montrose FC v Dumbarton 19/11/1966 | View match |