| Woking FC v Chelsea FC 05/08/1996 | View match | |
| Chelsea FC v PSV Eindhoven 11/08/1996 | View match | |
| Southampton FC v Chelsea FC 18/08/1996 | £2.00 | |
| Southampton FC v Chelsea FC 18/08/1996 | £4.50 | |
| Chelsea FC v Middlesbrough FC 21/08/1996 | £3.50 | |
| Chelsea FC v Coventry City FC 24/08/1996 | £3.50 | |
| Arsenal FC v Chelsea FC 04/09/1996 | £4.50 | |
| Sheffield Wednesday FC v Chelsea FC 07/09/1996 | £2.50 | |
| Chelsea FC v Aston Villa FC 15/09/1996 | £3.50 | |
| Chelsea FC v Aston Villa FC 15/09/1996 | £4.00 | |
| Chelsea FC v Aston Villa FC 15/09/1996 | £4.00 | |
| Blackpool FC v Chelsea FC 18/09/1996 | View match |