| Chelsea FC v Tottenham Hotspur FC 16/08/1988 | £5.50 | |
| Chelsea FC v Blackburn Rovers FC 27/08/1988 | £4.50 | |
| Chelsea FC v Blackburn Rovers FC 27/08/1988 | £4.00 | |
| Crystal Palace FC v Chelsea FC 30/08/1988 | £4.50 | |
| Chelsea FC v Oxford United FC 10/09/1988 | £4.00 | |
| Chelsea FC v Oxford United FC 10/09/1988 | £4.50 | |
| Chelsea FC v Manchester City FC 20/09/1988 | £4.50 | |
| Chelsea FC v Manchester City FC 20/09/1988 | £4.00 | |
| Chelsea FC v Leicester City FC 01/10/1988 | £4.50 | |
| Chelsea FC v Walsall FC 04/10/1988 | £4.50 | |
| Chelsea FC v Scunthorpe United FC 12/10/1988 | £4.50 | |
| Oldham Athletic FC v Chelsea FC 15/10/1988 | £4.50 |