| Chelsea FC v Sheffield Wednesday FC 15/09/1965 | £1.99 | |
| Chelsea FC v Roma (AS) 22/09/1965 | £5.50 | |
| Chelsea FC v Wiener Sports Club 01/12/1965 | £6.50 | |
| Tottenham Hotspur FC v Chelsea FC 11/12/1965 | £3.50 | |
| Chelsea FC v Fulham FC 05/02/1966 | £3.50 | |
| 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 | £3.50 | |
| Chelsea FC v TSV 1860 Munich 29/03/1966 | £6.50 | |
| Chelsea FC v West Ham United FC 09/04/1966 | £1.50 | |
| Chelsea FC v West Ham United FC 09/04/1966 | £4.00 |