| Swindon Town FC v Chelsea FC 09/05/1986 | View match | |
| Dundalk FC v Chelsea FC 02/08/1986 | View match | |
| Chelsea FC v Norwich City FC 23/08/1986 | £2.00 | |
| Chelsea FC v Norwich City FC 23/08/1986 | £3.50 | |
| Oxford United FC v Chelsea FC 25/08/1986 | £4.50 | |
| Sheffield Wednesday FC v Chelsea FC 30/08/1986 | £3.50 | |
| Chelsea FC v Coventry City FC 02/09/1986 | £3.00 | |
| Chelsea FC v Coventry City FC 02/09/1986 | £2.50 | |
| 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 |