| Chelsea FC v Portsmouth FC 17/08/2008 | £5.00 | |
| Wigan Athletic FC v Chelsea FC 24/08/2008 | £5.50 | |
| Chelsea FC v Tottenham Hotspur FC 31/08/2008 | £4.80 | |
| Chelsea FC v Tottenham Hotspur FC 31/08/2008 | £7.50 | |
| Manchester City FC v Chelsea FC 13/09/2008 | £6.00 | |
| Chelsea FC v Bordeaux 16/09/2008 | £5.20 | |
| Chelsea FC v Manchester United FC 21/09/2008 | £6.50 | |
| Portsmouth FC v Chelsea FC 24/09/2008 | £4.90 | |
| Stoke City FC v Chelsea FC 27/09/2008 | £5.50 | |
| CFR Cluj-Napoca v Chelsea FC 01/10/2008 | View match | |
| Chelsea FC v Aston Villa FC 05/10/2008 | £5.70 | |
| Middlesbrough FC v Chelsea FC 18/10/2008 | £6.50 |