| AFC Bournemouth v Chelsea FC 03/09/1988 | View match | |
| Chelsea FC v Oxford United FC 10/09/1988 | £4.50 | |
| Barnsley FC v Chelsea FC 17/09/1988 | View match | |
| Chelsea FC v Manchester City FC 20/09/1988 | £4.50 | |
| Chelsea FC v Manchester City FC 20/09/1988 | £4.00 | |
| Leeds United FC v Chelsea FC 24/09/1988 | View match | |
| Scunthorpe United FC v Chelsea FC 27/09/1988 | View match | |
| Chelsea FC v Leicester City FC 01/10/1988 | £4.50 | |
| Chelsea FC v Walsall FC 04/10/1988 | £4.50 | |
| Swindon Town FC v Chelsea FC 09/10/1988 | £4.50 | |
| Chelsea FC v Scunthorpe United FC 12/10/1988 | £4.50 | |
| Oldham Athletic FC v Chelsea FC 15/10/1988 | £4.50 |