| West Ham United FC v Chelsea FC 02/05/1988 | View match | |
| Chelsea FC v Charlton Athletic FC 07/05/1988 | £3.00 | |
| Chelsea FC v Charlton Athletic FC 07/05/1988 | £4.00 | |
| Blackburn Rovers FC v Chelsea FC 15/05/1988 | View match | |
| Chelsea FC v Blackburn Rovers FC 18/05/1988 | £4.50 | |
| Middlesbrough FC v Chelsea FC 25/05/1988 | View match | |
| Chelsea FC v Middlesbrough FC 28/05/1988 | £5.50 | |
| Chelsea FC v Tottenham Hotspur FC 16/08/1988 | View match | |
| Chelsea FC v Blackburn Rovers FC 27/08/1988 | £4.50 | |
| Crystal Palace FC v Chelsea FC 30/08/1988 | £4.50 | |
| AFC Bournemouth v Chelsea FC 03/09/1988 | View match | |
| Chelsea FC v Oxford United FC 10/09/1988 | £4.50 |