| Dumbarton v Aberdeen FC 05/03/1966 | View match | |
| Dumbarton v Queens Park FC 09/03/1966 | View match | |
| Montrose FC v Dumbarton 12/03/1966 | View match | |
| Dumbarton v Albion Rovers FC 19/03/1966 | View match | |
| Airdrieonians (Old) v Dumbarton 23/03/1966 | View match | |
| Dumbarton v Raith Rovers FC 26/03/1966 | View match | |
| Dumbarton v Ayr United FC 30/03/1966 | View match | |
| Queens Park FC v Dumbarton 05/04/1966 | View match | |
| Forfar Athletic FC v Dumbarton 09/04/1966 | View match | |
| Dumbarton v Queen Of The South FC 16/04/1966 | View match | |
| East Fife FC v Dumbarton 20/04/1966 | View match | |
| Alloa Athletic FC v Dumbarton 23/04/1966 | View match |