| Chelsea FC v Sheffield Wednesday FC 15/08/1987 | View match | |
| Portsmouth FC v Chelsea FC 18/08/1987 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 22/08/1987 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 22/08/1987 | £3.00 | |
| Chelsea FC v Real Sociedad 25/08/1987 | View match | |
| Chelsea FC v Luton Town FC 29/08/1987 | £3.50 | |
| Manchester United FC v Chelsea FC 31/08/1987 | £4.50 | |
| Manchester United FC v Chelsea FC 31/08/1987 | £3.00 | |
| Chelsea FC v Nottingham Forest FC 05/09/1987 | £3.50 | |
| Queens Park Rangers FC v Chelsea FC 12/09/1987 | £4.50 | |
| Chelsea FC v Norwich City FC 19/09/1987 | £3.50 | |
| Reading FC v Chelsea FC 23/09/1987 | £4.50 |