| Chelsea FC v Southend United FC 03/01/2009 | £5.50 | |
| Manchester United FC v Chelsea FC 11/01/2009 | £5.00 | |
| Chelsea FC v Middlesbrough FC 28/01/2009 | £4.80 | |
| Liverpool FC v Chelsea FC 01/02/2009 | £4.80 | |
| Chelsea FC v Hull City FC 07/02/2009 | £4.80 | |
| Watford FC v Chelsea FC 14/02/2009 | £4.80 | |
| Chelsea FC v Juventus FC 25/02/2009 | £4.80 | |
| Chelsea FC v Wigan Athletic FC 28/02/2009 | £4.80 | |
| Chelsea FC v Manchester City FC 15/03/2009 | £4.90 | |
| Tottenham Hotspur FC v Chelsea FC 21/03/2009 | £4.80 | |
| Newcastle United FC v Chelsea FC 04/04/2009 | £6.50 | |
| Liverpool FC v Chelsea FC 08/04/2009 | £6.50 |