| West Ham United FC v Chelsea FC 02/05/1988 | £4.50 | |
| Chelsea FC v Charlton Athletic FC 07/05/1988 | £3.00 | |
| Chelsea FC v Charlton Athletic FC 07/05/1988 | £4.00 | |
| Chelsea FC v Blackburn Rovers FC 18/05/1988 | £4.50 | |
| Chelsea FC v Middlesbrough FC 28/05/1988 | £5.50 | |
| Chelsea FC v Blackburn Rovers FC 27/08/1988 | £4.50 | |
| Crystal Palace FC v Chelsea FC 30/08/1988 | £4.50 | |
| Chelsea FC v Oxford United FC 10/09/1988 | £4.50 | |
| Chelsea FC v Manchester City FC 20/09/1988 | £4.50 | |
| Leeds United FC v Chelsea FC 24/09/1988 | £4.50 | |
| Chelsea FC v Leicester City FC 01/10/1988 | £4.50 | |
| Chelsea FC v Walsall FC 04/10/1988 | £4.50 |