| 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 | |
| Chelsea FC v Fulham FC 05/02/1966 | £3.50 | |
| AC Milan v Chelsea FC 09/02/1966 | View match | |
| Chelsea FC v Leeds United FC 12/02/1966 | £5.00 | |
| Chelsea FC v AC Milan 16/02/1966 | £6.50 | |
| Chelsea FC v Arsenal FC 19/02/1966 | £4.00 |