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| July 2008 | ||||
|---|---|---|---|---|
| 12 Jul | Pre-season | Aberdeen | A | 2-0 |
| 19 Jul | Pre-season | Kaizer Chiefs | N | 1-1 |
| 22 Jul | Pre-season | Orlando Pirates | N | 2-0 |
| 26 Jul | Pre-season | Kaizer Chiefs | N | 4-0 |
| 27 Jul | Pre-season | Portsmouth | N | 2-1 |
| August 2008 | ||||
| 02 Aug | Pre-season | RCD Espanyol | H | 1-0 |
| 04 Aug | Pre-season | Peterborough | A | 2-0 |
| 06 Aug | Pre-season | Juventus | H | 0-0 |
| 10 Aug | Community Shield | Portsmouth | N | 0(3)-0(1) |
| 17 Aug | Premiership | Newcastle | H | 1-1 |
| 25 Aug | Premiership | Portsmouth | A | 1-0 |
| 29 Aug | UEFA Super Cup | Zenit St Petersburg | N | 1-2 |
| September 2008 | ||||
| 13 Sep | Premiership | Liverpool | A | 1-2 |
| 17 Sep | Champions League | Villarreal | H | 0-0 |
| 21 Sep | Premiership | Chelsea | A | 1-1 |
| 23 Sep | Carling Cup | Middlesbrough | H | 3-1 |
| 27 Sep | Premiership | Bolton | H | 2-0 |
| 30 Sep | Champions League | Aalborg BK | A | 3-0 |
| October 2008 | ||||
| 04 Oct | Premiership | Blackburn | A | 2-0 |
| 18 Oct | Premiership | West Brom | H | 4-0 |
| 21 Oct | Champions League | Celtics | H | 3-0 |
| 25 Oct | Premiership | Everton | A | 1-1 |
| 29 Oct | Premiership | West Ham | H | 2-0 |
| November 2008 | ||||
| 01 Nov | Premiership | Hull City | H | 4-3 |
| 05 Nov | Champions League | Celtics | A | 1-1 |
| 08 Nov | Premiership | Arsenal | A | 1-2 |
| 11 Nov | Carling Cup | PQR | H | 1-0 |
| 15 Nov | Premiership | Stoke City | H | 5-0 |
| 22 Nov | Premiership | Aston Villa | A | 0-0 |
| 25 Nov | Champions League | Villarreal | A | 0-0 |
| 30 Nov | Premiership | Man City | A | 1-0 |
| December 2008 | ||||
| 03 Dec | Carling Cup | Blackburn | H | 5-3 |
| 06 Dec | Premiership | Sunderland | H | - |
| 10 Dec | Champions League | Aalborg BK | H | - |
| 13 Dec | Premiership | Tottenham | A | - |
| 20 Dec | Premiership | Wigan | H | - |
| 26 Dec | Premiership | Stoke City | A | - |
| 28 Dec | Premiership | Middlesbro | H | - |
| January 2009 | ||||
| 04 Jan | FA Cup | Southampton | A | - |
| 10 Jan | Premiership | Chelsea | H | - |
| 17 Jan | Premiership | Bolton | A | - |
| 27 Jan | Premiership | West Brom | A | - |
| 31 Jan | Premiership | Everton | H | - |
| February 2009 | ||||
| 07 Feb | Premiership | West Ham | A | - |
| 21 Feb | Premiership | Blackburn | H | - |
| 28 Feb | Premiership | Portsmouth | H | - |
| March 2009 | ||||
| 04 Mar | Premiership | Newcastle | A | - |
| 14 Mar | Premiership | Liverpool | H | - |
| 21 Mar | Premiership | Fulham | A | - |
| April 2009 | ||||
| 04 Apr | Premiership | Aston Villa | H | - |
| 11 Apr | Premiership | Sunderland | A | - |
| 18 Apr | Premiership | Wigan | A | - |
| 25 Apr | Premiership | Tottenham | H | - |
| May 2009 | ||||
| 02 May | Premiership | Middlesbro | A | - |
| 09 May | Premiership | Man City | H | - |
| 16 May | Premiership | Arsenal | H | - |
| 24 May | Premiership | Hull City | A | - |
07-08 Season: Premier and European League Champions
06-07 Season: Premier Champions