| East Fife FC v Forfar Athletic FC 09/10/1965 | View match | |
| Alloa Athletic FC v East Fife FC 16/10/1965 | View match | |
| East Fife FC v Cowdenbeath FC 23/10/1965 | View match | |
| Stranraer v East Fife FC 30/10/1965 | View match | |
| East Fife FC v Arbroath FC 06/11/1965 | View match | |
| Third Lanark v East Fife FC 13/11/1965 | View match | |
| East Fife FC v Brechin City FC 20/11/1965 | View match | |
| East Fife FC v Airdrieonians (Old) 11/12/1965 | View match | |
| Montrose FC v East Fife FC 18/12/1965 | View match | |
| East Fife FC v Stenhousemuir FC 25/12/1965 | View match | |
| Albion Rovers FC v East Fife FC 03/01/1966 | View match | |
| East Stirlingshire FC v East Fife FC 08/01/1966 | View match |