| Raith Rovers FC v Hibernian FC 14/11/1959 | View match | |
| Hibernian FC v Dundee 21/11/1959 | View match | |
| Hibernian FC v Stirling Albion FC 28/11/1959 | View match | |
| Arbroath FC v Hibernian FC 05/12/1959 | View match | |
| Partick Thistle FC v Hibernian FC 10/12/1959 | View match | |
| Hibernian FC v Ayr United FC 12/12/1959 | View match | |
| Aberdeen FC v Hibernian FC 26/12/1959 | View match | |
| Hibernian FC v Heart Of Midlothian (Hearts) 01/01/1960 | View match | |
| Rangers (Glasgow) FC v Hibernian FC 02/01/1960 | View match | |
| Hibernian FC v Third Lanark 09/01/1960 | View match | |
| Kilmarnock FC v Hibernian FC 16/01/1960 | View match | |
| Hibernian FC v Clyde 23/01/1960 | View match |