| Cowdenbeath FC v East Fife FC 13/04/1966 | View match | |
| Airdrieonians (Old) v East Fife FC 16/04/1966 | View match | |
| East Fife FC v Dumbarton 20/04/1966 | View match | |
| East Fife FC v Montrose FC 23/04/1966 | View match | |
| Ayr United FC v East Fife FC 27/04/1966 | View match | |
| Stenhousemuir FC v East Fife FC 30/04/1966 | View match | |
| Morton FC v East Fife FC 13/08/1966 | View match | |
| East Fife FC v Arbroath FC 17/08/1966 | View match | |
| East Fife FC v Third Lanark 20/08/1966 | View match | |
| Brechin City FC v East Fife FC 24/08/1966 | View match | |
| East Fife FC v Morton FC 27/08/1966 | View match | |
| Arbroath FC v East Fife FC 31/08/1966 | View match |