| 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 | |
| Chelsea FC v Blackburn Rovers FC 18/12/1965 | View match | |
| Northampton Town FC v Chelsea FC 27/12/1965 | View match | |
| Chelsea FC v Northampton Town FC 28/12/1965 | View match | |
| Blackpool FC v Chelsea FC 01/01/1966 | View match | |
| Chelsea FC v Tottenham Hotspur FC 08/01/1966 | View match | |
| Liverpool FC v Chelsea FC 22/01/1966 | View match | |
| Burnley FC v Chelsea FC 29/01/1966 | View match |