| Dumbarton v Montrose FC 13/11/1965 | View match | |
| Raith Rovers FC v Dumbarton 27/11/1965 | View match | |
| Queen Of The South FC v Dumbarton 11/12/1965 | View match | |
| Dumbarton v Alloa Athletic FC 18/12/1965 | View match | |
| Cowdenbeath FC v Dumbarton 25/12/1965 | View match | |
| Dumbarton v Third Lanark 03/01/1966 | View match | |
| Dumbarton v Brechin City FC 15/01/1966 | View match | |
| Dumbarton v Stenhousemuir FC 25/01/1966 | View match | |
| Dumbarton v Montrose FC 09/02/1966 | View match | |
| East Stirlingshire FC v Dumbarton 12/02/1966 | View match | |
| Dumbarton v Queen Of The South FC 23/02/1966 | View match | |
| Arbroath FC v Dumbarton 26/02/1966 | View match |