| Leicester City FC v Chelsea FC 21/03/1966 | View match | |
| Chelsea FC v Hull City FC 26/03/1966 | View match | |
| Chelsea FC v TSV 1860 Munich 29/03/1966 | £6.50 | |
| Hull City FC v Chelsea FC 31/03/1966 | View match | |
| Leeds United FC v Chelsea FC 04/04/1966 | View match | |
| Chelsea FC v West Ham United FC 09/04/1966 | £4.50 | |
| Chelsea FC v West Ham United FC 09/04/1966 | £1.50 | |
| Chelsea FC v West Ham United FC 09/04/1966 | £4.00 | |
| Chelsea FC v Nottingham Forest FC 11/04/1966 | £4.50 | |
| Nottingham Forest FC v Chelsea FC 12/04/1966 | View match | |
| Sunderland FC v Chelsea FC 16/04/1966 | View match | |
| Chelsea FC v Sheffield Wednesday FC 23/04/1966 | £7.50 |