| 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 | |
| Chelsea FC v Sunderland FC 22/02/1966 | £6.50 | |
| 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 |