| Stranraer v Brechin City FC 03/09/1966 | View match | |
| Hamilton Academicals v Stranraer 07/09/1966 | View match | |
| Stranraer v Queen Of The South FC 10/09/1966 | View match | |
| Stranraer v Hamilton Academicals 14/09/1966 | View match | |
| Queens Park FC v Stranraer 17/09/1966 | View match | |
| East Stirlingshire FC v Stranraer 21/09/1966 | View match | |
| Stranraer v Alloa Athletic FC 24/09/1966 | View match | |
| Montrose FC v Stranraer 01/10/1966 | View match | |
| Stranraer v Forfar Athletic FC 08/10/1966 | View match | |
| Cowdenbeath FC v Stranraer 15/10/1966 | View match | |
| Stranraer v Dumbarton 22/10/1966 | View match | |
| Stranraer v Clydebank FC (Old) 29/10/1966 | View match |