| Chelsea FC v Luton Town FC 06/09/1986 | £3.50 | |
| Tottenham Hotspur FC v Chelsea FC 13/09/1986 | View match | |
| Tottenham Hotspur FC v Chelsea FC 13/09/1986 | £5.00 | |
| Chelsea FC v Nottingham Forest FC 20/09/1986 | £3.50 | |
| Chelsea FC v Nottingham Forest FC 20/09/1986 | £3.00 | |
| York City FC v Chelsea FC 23/09/1986 | View match | |
| Manchester United FC v Chelsea FC 28/09/1986 | View match | |
| Watford FC v Chelsea FC 29/09/1986 | View match | |
| Chelsea FC v Charlton Athletic FC 04/10/1986 | £3.00 | |
| Chelsea FC v Charlton Athletic FC 04/10/1986 | £4.00 | |
| Chelsea FC v Charlton Athletic FC 04/10/1986 | £3.50 | |
| Chelsea FC v York City FC 08/10/1986 | £5.00 |