| East Fife FC v Queens Park FC 12/12/1959 | View match | |
| East Fife FC v Stranraer 19/12/1959 | View match | |
| Dundee United FC v East Fife FC 26/12/1959 | View match | |
| East Fife FC v Cowdenbeath FC 01/01/1960 | View match | |
| Queen Of The South FC v East Fife FC 02/01/1960 | View match | |
| East Fife FC v Albion Rovers FC 09/01/1960 | View match | |
| Morton FC v East Fife FC 16/01/1960 | View match | |
| East Fife FC v Partick Thistle FC 30/01/1960 | View match | |
| Berwick Rangers FC v East Fife FC 13/02/1960 | View match | |
| East Fife FC v Stenhousemuir FC 20/02/1960 | View match | |
| East Fife FC v Falkirk FC 27/02/1960 | View match | |
| Brechin City FC v East Fife FC 05/03/1960 | View match |