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| Current League Position | League Position Analysis | Squad Statistics |
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| Bolton Wanderers | 3 | 1 | Stoke City | 16/08/2008 |
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| Newcastle United | 1 | 0 | Bolton Wanderers | 23/08/2008 |
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| Bolton Wanderers | 0 | 0 | West Bromwich Albion | 30/08/2008 |
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| Fulham | 2 | 1 | Bolton Wanderers | 13/09/2008 |
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| Bolton Wanderers | 1 | 3 | Arsenal | 20/09/2008 |
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| Manchester United | 2 | 0 | Bolton Wanderers | 27/09/2008 |
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| West Ham United | 1 | 3 | Bolton Wanderers | 05/10/2008 |
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| Bolton Wanderers | 0 | 0 | Blackburn Rovers | 18/10/2008 |
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| Tottenham Hotspur | 2 | 0 | Bolton Wanderers | 26/10/2008 |
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| Bolton Wanderers | 0 | 1 | Everton | 29/10/2008 |
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| Bolton Wanderers | 2 | 0 | Manchester City | 02/11/2008 |
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| Hull City | 0 | 1 | Bolton Wanderers | 08/11/2008 |
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| Bolton Wanderers | 0 | 2 | Liverpool | 15/11/2008 |
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| Middlesbrough | 1 | 3 | Bolton Wanderers | 22/11/2008 |
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| Sunderland | 1 | 4 | Bolton Wanderers | 29/11/2008 |
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| Bolton Wanderers | 0 | 2 | Chelsea | 06/12/2008 |
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| Aston Villa | 4 | 2 | Bolton Wanderers | 13/12/2008 |
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| Bolton Wanderers | 2 | 1 | Portsmouth | 20/12/2008 |
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| Liverpool | 3 | 0 | Bolton Wanderers | 26/12/2008 |
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| Bolton Wanderers | 0 | 1 | Wigan Athletic | 28/12/2008 |
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| Arsenal | 1 | 0 | Bolton Wanderers | 10/01/2009 |
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| Bolton Wanderers | 0 | 1 | Manchester United | 17/01/2009 |
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| Blackburn Rovers | 2 | 2 | Bolton Wanderers | 28/01/2009 |
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| Bolton Wanderers | 3 | 2 | Tottenham Hotspur | 31/01/2009 |
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| Everton | 3 | 0 | Bolton Wanderers | 07/02/2009 |
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| Bolton Wanderers | 2 | 1 | West Ham United | 21/02/2009 |
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| Bolton Wanderers | 1 | 0 | Newcastle United | 01/03/2009 |
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| Stoke City | 2 | 0 | Bolton Wanderers | 04/03/2009 |
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| Bolton Wanderers | 1 | 3 | Fulham | 14/03/2009 |
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| West Bromwich Albion | 1 | 1 | Bolton Wanderers | 21/03/2009 |
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| Bolton Wanderers | 4 | 1 | Middlesbrough | 04/04/2009 |
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| Chelsea | 4 | 3 | Bolton Wanderers | 11/04/2009 |
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| Portsmouth | 1 | 0 | Bolton Wanderers | 18/04/2009 |
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| Bolton Wanderers | 1 | 1 | Aston Villa | 25/04/2009 |
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| Wigan Athletic | 0 | 0 | Bolton Wanderers | 02/05/2009 |
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| Bolton Wanderers | 0 | 0 | Sunderland | 09/05/2009 |
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| Bolton Wanderers | 1 | 1 | Hull City | 16/05/2009 |
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| Manchester City | 1 | 0 | Bolton Wanderers | 24/05/2009 |
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