| League | Date | Home Team | Score | Away Team |
|---|---|---|---|---|
| PL | 24-05-2009 | Sunderland | 2 - 3 | Chelsea |
| PL | 17-05-2009 | Chelsea | 2 - 0 | Blackburn |
| PL | 10-05-2009 | Arsenal | 1 - 4 | Chelsea |
| PL | 02-05-2009 | Chelsea | 3 - 1 | Fulham |
| PL | 25-04-2009 | West Ham | 0 - 1 | Chelsea |
| PL | 22-04-2009 | Chelsea | 0 - 0 | Everton |
| PL | 11-04-2009 | Chelsea | 4 - 3 | Bolton |
| PL | 04-04-2009 | Newcastle | 0 - 2 | Chelsea |
| PL | 21-03-2009 | Tottenham | 1 - 0 | Chelsea |
| PL | 15-03-2009 | Chelsea | 1 - 0 | Man City |
| PL | 03-03-2009 | Portsmouth | 0 - 1 | Chelsea |
| PL | 28-02-2009 | Chelsea | 2 - 1 | Wigan |
| PL | 21-02-2009 | Aston Villa | 0 - 1 | Chelsea |
| PL | 07-02-2009 | Chelsea | 0 - 0 | Hull |
| PL | 01-02-2009 | Liverpool | 2 - 0 | Chelsea |
| PL | 28-01-2009 | Chelsea | 2 - 0 | Middlesbrough |
| PL | 17-01-2009 | Chelsea | 2 - 1 | Stoke |
| PL | 11-01-2009 | Man United | 3 - 0 | Chelsea |
| PL | 28-12-2008 | Fulham | 2 - 2 | Chelsea |
| PL | 26-12-2008 | Chelsea | 2 - 0 | West Brom |
| PL | 22-12-2008 | Everton | 0 - 0 | Chelsea |
| PL | 14-12-2008 | Chelsea | 1 - 1 | West Ham |
| PL | 06-12-2008 | Bolton | 0 - 2 | Chelsea |
| PL | 30-11-2008 | Chelsea | 1 - 2 | Arsenal |
| PL | 22-11-2008 | Chelsea | 0 - 0 | Newcastle |
| PL | 15-11-2008 | West Brom | 0 - 3 | Chelsea |
| PL | 09-11-2008 | Blackburn | 0 - 2 | Chelsea |
| PL | 01-11-2008 | Chelsea | 5 - 0 | Sunderland |
| PL | 29-10-2008 | Hull | 0 - 3 | Chelsea |
| PL | 26-10-2008 | Chelsea | 0 - 1 | Liverpool |
| PL | 18-10-2008 | Middlesbrough | 0 - 5 | Chelsea |
| PL | 05-10-2008 | Chelsea | 2 - 0 | Aston Villa |
| PL | 27-09-2008 | Stoke | 0 - 2 | Chelsea |
| PL | 21-09-2008 | Chelsea | 1 - 1 | Man United |
| PL | 13-09-2008 | Man City | 1 - 3 | Chelsea |
| PL | 31-08-2008 | Chelsea | 1 - 1 | Tottenham |
| PL | 24-08-2008 | Wigan | 0 - 1 | Chelsea |
| PL | 17-08-2008 | Chelsea | 4 - 0 | Portsmouth |