| Hamburg SV v Chelsea FC 12/08/1966 | View match | |
| West Ham United FC v Chelsea FC 20/08/1966 | View match | |
| Chelsea FC v Nottingham Forest FC 24/08/1966 | £2.50 | |
| Chelsea FC v Nottingham Forest FC 24/08/1966 | £4.00 | |
| Chelsea FC v Sheffield Wednesday FC 27/08/1966 | £3.50 | |
| Chelsea FC v Sheffield Wednesday FC 27/08/1966 | £3.00 | |
| Nottingham Forest FC v Chelsea FC 30/08/1966 | View match | |
| Southampton FC v Chelsea FC 03/09/1966 | View match | |
| Chelsea FC v Leicester City FC 07/09/1966 | £3.50 | |
| Chelsea FC v Leicester City FC 07/09/1966 | £3.50 | |
| Chelsea FC v Sunderland FC 10/09/1966 | £4.00 | |
| Chelsea FC v Sunderland FC 10/09/1966 | £3.00 |