| Swindon Town FC v Chelsea FC 13/01/1988 | View match | |
| Sheffield Wednesday FC v Chelsea FC 16/01/1988 | £3.50 | |
| Swindon Town FC v Chelsea FC 19/01/1988 | £5.50 | |
| Chelsea FC v Portsmouth FC 23/01/1988 | View match | |
| Manchester United FC v Chelsea FC 30/01/1988 | £4.50 | |
| Nottingham Forest FC v Chelsea FC 06/02/1988 | £3.50 | |
| Chelsea FC v Manchester United FC 13/02/1988 | View match | |
| Newcastle United FC v Chelsea FC 27/02/1988 | View match | |
| Coventry City FC v Chelsea FC 05/03/1988 | £3.50 | |
| Chelsea FC v Everton FC 12/03/1988 | £3.50 | |
| Oxford United FC v Chelsea FC 19/03/1988 | £4.50 | |
| Chelsea FC v Southampton FC 26/03/1988 | £4.50 |