| Blackburn Rovers FC v Chelsea FC 16/10/1965 | View match | |
| Chelsea FC v Leicester City FC 23/10/1965 | View match | |
| Sheffield United FC v Chelsea FC 30/10/1965 | View match | |
| Chelsea FC v Leeds United FC 06/11/1965 | View match | |
| West Ham United FC v Chelsea FC 13/11/1965 | View match | |
| Wiener Sports Club v Chelsea FC 17/11/1965 | View match | |
| Aston Villa FC v Chelsea FC 27/11/1965 | View match | |
| Chelsea FC v Wiener Sports Club 01/12/1965 | £6.50 | |
| Chelsea FC v Liverpool FC 04/12/1965 | View match | |
| Tottenham Hotspur FC v Chelsea FC 11/12/1965 | View match | |
| Chelsea FC v Blackburn Rovers FC 18/12/1965 | View match | |
| Chelsea FC v Blackburn Rovers FC 18/12/1965 | View match |