| 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 | |
| Chelsea FC v Plymouth Argyle FC 22/10/1988 | £5.50 | |
| Hull City FC v Chelsea FC 25/10/1988 | £4.50 | |
| Chelsea FC v Brighton & Hove Albion FC 29/10/1988 | £4.00 | |
| Chelsea FC v Brighton & Hove Albion FC 29/10/1988 | £4.50 | |
| Chelsea FC v Plymouth Argyle FC 09/11/1988 | £8.50 | |
| Chelsea FC v Sunderland FC 12/11/1988 | £5.50 | |
| Bradford City FC v Chelsea FC 19/11/1988 | £4.50 | |
| Chelsea FC v Shrewsbury Town FC 26/11/1988 | £4.50 | |
| Chelsea FC v Shrewsbury Town FC 26/11/1988 | £4.00 |