| Match date | Home / Away | Opponent | Competition | Score | PL Points | |
| July 2008 | ||||||
| 14 Mon | Neutral | Tavarnes | Pre-Season friendly | 8-0 | ||
| 19 Sat | Away | CD Atletico Denia | Pre-Season friendly | 2-4 | ||
| 24 Thu | Away | Hercules CF | Pre-Season friendly | 1-1 | ||
| 28 Mon | Away | Norwich City | Pre-Season friendly | 1-5 | ||
| 30 Wed | Away | Leyton Orient | Pre-Season friendly | 1-5 | ||
| August 2008 | ||||||
| 01 Fri | Neutral | Celtic | Feyenoord Centenary | Pre-Season friendly | 2-0 | |
| 03 Sun | Neutral | Borussia Dortmund | Feyenoord Centenary | Pre-Season friendly | 3-0 | |
| 10 Sun | Home | AS Roma | Pre-Season friendly | 5-0 | ||
| 16 Sat | Away | Middlesbrough | Barclays Premier League | Matchday 1 | 2-1 | 0 |
| 23 Sat | Home | Sunderland | Barclays Premier League | Matchday 2 | 1-2 | 0 |
| 31 Sun | Away | Chelsea | Barclays Premier League | Matchday 3 | 1-1 | 1 |
| September 2008 | ||||||
| 15 Mon | Home | Aston Villa | Barclays Premier League | Matchday 4 | 1-2 | 1 |
| 18 Thu | Home | Wisla Krakow | UEFA Cup | Round 1 1st leg | 2-1 | |
| 21 Sun | Home | Wigan Athletic | Barclays Premier League | Matchday 5 | 0-0 | 2 |
| 24 Wed | Away | Newcastle United | League cup | Round 3 | 1-2 | |
| 28 Sun | Away | Portsmouth | Barclays Premier League | Matchday 6 | 2-0 | 2 |
| October 2008 | ||||||
| 02 Thu | Away | Wisla Krakow | UEFA Cup | Round 1 2nd leg | 1-1 | |
| 05 Sun | Home | Hull City | Barclays Premier League | Matchday 7 | 0-1 | 2 |
| 19 Sun | Away | Stoke City | Barclays Premier League | Matchday 8 | 2-1 | 2 |
| 23 Thu | Away | Udinese | UEFA Cup | Group 1 | 2-0 | |
| 26 Sun | Home | Bolton Wanderers | Barclays Premier League | Matchday 9 | 2-0 | 5 |
| 29 Wed | Away | Arsenal | Barclays Premier League | Matchday 10 | 4-4 | 6 |
| November 2008 | ||||||
| 01 Sat | Home | Liverpool | Barclays Premier League | Matchday 11 | 2-1 | 9 |
| 06 Thu | Home | Dinamo Zagreb | UEFA Cup | Group 2 | 4-0 | |
| 09 Sun | Away | Manchester City | Barclays Premier League | Matchday 12 | 1-2 | 12 |
| 12 Wed | Home | Liverpool | League cup | Round 4 | 4-2 | |
| 15 Sat | Away | Fulham | Barclays Premier League | Matchday 13 | 2-1 | 12 |
| 23 Sun | Home | Blackburn Rovers | Barclays Premier League | Matchday 14 | 1-0 | 15 |
| 27 Thu | Away | NEC Nijmegen | UEFA Cup | Group 3 | 0-1 | |
| 30 Sun | Home | Everton | Barclays Premier League | Matchday 15 | 0-1 | 15 |
| December 2008 | ||||||
| 03 Wed | Away | Watford | League cup | Round 5 | 1-2 | |
| 08 Mon | Away | West Ham United | Barclays Premier League | Matchday 16 | 0-2 | 18 |
| 13 Sat | Home | Manchester United | Barclays Premier League | Matchday 17 | 0-0 | 19 |
| 18 Thu | Home | Spartak Moscow | UEFA Cup | Group 4 | 2-2 | |
| 21 Sun | Away | Newcastle United | Barclays Premier League | Matchday 18 | 2-1 | 19 |
| 26 Fri | Home | Fulham | Barclays Premier League | Matchday 19 | 0-0 | 20 |
| 28 Sun | Away | West Bromwich Albion | Barclays Premier League | Matchday 20 | 2-0 | 20 |
| January 2009 | ||||||
| 02 Fri | Home | Wigan Athletic | FA Cup | Round 3 | 3-1 | |
| 06 Tue | Home | Burnley | League cup | S/F 1st leg | 4-1 | |
| 11 Sun | Away | Wigan Athletic | Barclays Premier League | Matchday 21 | 1-0 | 20 |
| 18 Sun | Home | Portsmouth | Barclays Premier League | Matchday 22 | 1-1 | 21 |
| 21 Wed | Away | Burnley | League cup | S/F 2nd leg | 3-2 | |
| 24 Sat | Away | Manchester United | FA Cup | Round 4 | 2-1 | |
| 27 Tue | Home | Stoke City | Barclays Premier League | Matchday 23 | 3-1 | 24 |
| 31 Sat | Away | Bolton Wanderers | Barclays Premier League | Matchday 24 | 3-2 | 24 |
| February 2009 | ||||||
| 08 Sun | Home | Arsenal | Barclays Premier League | Matchday 25 | 0-0 | 25 |
| 19 Thu | Away | Shakhtar Donetsk | UEFA Cup | Round of 32 1st leg | 2-0 | |
| 23 Mon | Away | Hull City | Barclays Premier League | Matchday 26 | 1-2 | 28 |
| 26 Thu | Home | Shakhtar Donetsk | UEFA Cup | Round of 32 2nd leg | 1-1 | |
| March 2009 | ||||||
| 01 Sun | Wembley | Manchester United | League cup | Final | 0-0 | |
| 04 Wed | Home | Middlesbrough | Barclays Premier League | Matchday 27 | 4-0 | 31 |
| 07 Sat | Away | Sunderland | Barclays Premier League | Matchday 28 | 1-1 | 32 |
| 15 Sun | Away | Aston Villa | Barclays Premier League | Matchday 29 | 1-2 | 35 |
| 21 Sat | Home | Chelsea | Barclays Premier League | Matchday 30 | 1-0 | 38 |
| April 2009 | ||||||
| 04 Sat | Away | Blackburn Rovers | Barclays Premier League | Matchday 31 | 2-1 | 38 |
| 11 Sat | Home | West Ham United | Barclays Premier League | Matchday 32 | 1-0 | 41 |
| 19 Sun | Home | Newcastle United | Barclays Premier League | Matchday 33 | 1-0 | 44 |
| 25 Sat | Away | Manchester United | Barclays Premier League | Matchday 34 | 5-2 | 44 |
| May 2009 | ||||||
| 02 Sat | Home | West Bromwich Albion | Barclays Premier League | Matchday 35 | 1-0 | 47 |
| 09 Sat | Away | Everton | Barclays Premier League | Matchday 36 | 0-0 | 48 |
| 16 Sat | Home | Manchester City | Barclays Premier League | Matchday 37 | 2-1 | 51 |
| 24 Sun | Away | Liverpool | Barclays Premier League | Matchday 38 | 3-1 | 51 |