2008 to 2009 League Fixtures - Portsmouth Football Club
| Date | Opponent | Venue | Result | Attendance | League Position |
|---|---|---|---|---|---|
| 17 Aug | Chelsea | Away | L 4 - 0 | 41,468 | 20th |
| 25 Aug | Manchester United | Home | L 0 - 1 | 20,540 | 20th |
| 30 Aug | Everton | Away | W 0 - 3 | 34,418 | 17th |
| 13 Sep | Middlesbrough | Home | W 2 - 1 | 19,425 | 9th |
| 21 Sep | Manchester City | Away | L 6 - 0 | 40,238 | 13th |
| 28 Sep | Tottenham Hotspur | Home | W 2 - 0 | 20,352 | 9th |
| 05 Oct | Stoke City | Home | W 2 - 1 | 19,248 | 7th |
| 18 Oct | Aston Villa | Away | D 0 - 0 | 37,660 | 7th |
| 26 Oct | Fulham | Home | D 1 - 1 | 19,233 | 7th |
| 29 Oct | Liverpool | Away | L 1 - 0 | 43,378 | 7th |
| 01 Nov | Wigan Athletic | Home | L 1 - 2 | 18,416 | 9th |
| 08 Nov | Sunderland | Away | W 1 - 2 | 37,712 | 9th |
| 15 Nov | West Ham United | Away | D 0 - 0 | 32,328 | 8th |
| 22 Nov | Hull City | Home | D 2 - 2 | 20,240 | 8th |
| 30 Nov | Blackburn Rovers | Home | W 3 - 2 | 18,111 | 8th |
| 07 Dec | West Bromwich Albion | Away | D 1 - 1 | 24,964 | 7th |
| 14 Dec | Newcastle United | Home | L 0 - 3 | 19,416 | 8th |
| 20 Dec | Bolton Wanderers | Away | L 2 - 1 | 19,884 | 10th |
| 26 Dec | West Ham United | Home | L 1 - 4 | 20,102 | 11th |
| 28 Dec | Arsenal | Away | L 1 - 0 | 60,092 | 12th |
| 18 Jan | Tottenham Hotspur | Away | D 1 - 1 | 36,011 | 12th |
| 27 Jan | Aston Villa | Home | L 0 - 1 | 19,073 | 14th |
| 31 Jan | Fulham | Away | L 3 - 1 | 23,722 | 16th |
| 07 Feb | Liverpool | Home | L 2 - 3 | 20,524 | 16th |
| 14 Feb | Manchester City | Home | W 2 - 0 | 20,018 | 15th |
| 21 Feb | Stoke City | Away | D 2 - 2 | 26,354 | 14th |
| 03 Mar | Chelsea | Home | L 0 - 1 | 20,326 | 16th |
| 14 Mar | Middlesbrough | Away | D 1 - 1 | 24,281 | 17th |
| 21 Mar | Everton | Home | W 2 - 1 | 20,388 | 15th |
| 04 Apr | Hull City | Away | D 0 - 0 | 24,802 | 16th |
| 11 Apr | West Bromwich Albion | Home | D 2 - 2 | 20,376 | 14th |
| 18 Apr | Bolton Wanderers | Home | W 1 - 0 | 20,158 | 14th |
| 22 Apr | Manchester United | Away | L 2 - 0 | 74,895 | 14th |
| 27 Apr | Newcastle United | Away | D 0 - 0 | 47,481 | 14th |
| 02 May | Arsenal | Home | L 0 - 3 | 20,418 | 14th |
| 09 May | Blackburn Rovers | Away | L 2 - 0 | 24,264 | 15th |
| 18 May | Sunderland | Home | W 3 - 1 | 20,398 | 14th |
| 24 May | Wigan Athletic | Away | L 1 - 0 | 17,696 | 14th |
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