| 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 | |
| Chelsea FC v Charlton Athletic FC 14/09/1966 | £10.00 | |
| Aston Villa FC v Chelsea FC 17/09/1966 | View match | |
| Chelsea FC v Arsenal FC 24/09/1966 | £4.00 | |
| Manchester City FC v Chelsea FC 01/10/1966 | View match |