| Chelsea FC v Sunderland FC 22/02/1966 | £3.50 | |
| Everton FC v Chelsea FC 26/02/1966 | View match | |
| AC Milan v Chelsea FC 02/03/1966 | View match | |
| Chelsea FC v Shrewsbury Town FC 05/03/1966 | View match | |
| Chelsea FC v Manchester United FC 12/03/1966 | View match | |
| TSV 1860 Munich v Chelsea FC 15/03/1966 | View match | |
| Newcastle United FC v Chelsea FC 19/03/1966 | View match | |
| 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 |