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| August 2008 |
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| CHAMP | 13 | FC PYUNIK | Away | 1 - 2 | Won | | | PREM | 16 | Sunderland | Home | 1 - 1 | Draw | 14th | | PREM | 23 | Fulham | Away | 1 - 1 | Draw | 14th | | CHAMP | 27 | FC PYUNIK | Home | 5 - 0 | Won | | | PREM | 30 | Bolton | Away | 1 - 2 | Won | 6th | | September 2008 |
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| PREM | 06 | Wigan | Home | 4 - 1 | Won | 3rd | | PREM | 13 | Newcastle | Away | 2 - 2 | Draw | 5th | | CHAMP | 16 | GALATASARAY | Away | 1 - 0 | Lost | 3rd of 4 | | PREM | 20 | Everton | Home | 1 - 2 | Lost | 7th | | CARLING | 24 | HEREFORD UTD | Home | 3 - 0 | Won | | | PREM | 27 | Blackburn | Away | 1 - 2 | Won | 6th | | CHAMP | 30 | BAYERN MUNICH | Home | 2 - 1 | Won | 3rd of 4 | | October 2008 |
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| PREM | 04 | Arsenal | Away | 2 - 3 | Won | 4th | | PREM | 11 | West Ham | Home | 4 - 3 | Won | 3rd | | PREM | 18 | Chelsea | Home | 1 - 1 | Draw | 4th | | CHAMP | 21 | DINAMO ZAGREB | Away | 1 - 1 | Draw | 3rd of 4 | | PREM | 25 | WBA | Away | 1 - 2 | Won | 3rd | | November 2008 |
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| PREM | 01 | Tottenham | Away | 1 - 3 | Won | 3rd | | CHAMP | 04 | DINAMO ZAGREB | Home | 2 - 2 | Draw | 3rd of 4 | | PREM | 08 | Manchester City | Home | 1 - 1 | Draw | 3rd | | CARLING | 12 | NEWCASTLE | Home | 1 - 0 | Won | | | PREM | 15 | Portsmouth | Away | 2 - 2 | Draw | 4th | | PREM | 22 | Stoke City | Away | 3 - 0 | Lost | 5th | | CHAMP | 25 | BAYERN MUNICH | Away | 2 - 0 | Lost | 3rd of 4 | | PREM | 29 | Middlesbrough | Home | 2 - 2 | Draw | 5th | | December 2008 |
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| CARLING | 02 | BLACKBURN ROVERS | Home | 2 - 1 | Won | | | PREM | 06 | Liverpool | Away | 2 - 1 | Lost | 6th | | CHAMP | 09 | GALATASARAY | Home | 2 - 2 | Draw | Qualify | | PREM | 13 | Aston Villa | Home | 1 - 1 | Draw | 7th | | PREM | 20 | Manchester Utd | Home | 0 - 3 | Lost | 8th | | PREM | 27 | Wigan | Away | 2 - 1 | Lost | 9th | | January 2009 |
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| FA CUP | 03 | MORECAMBE | Away | 1 - 2 | Won | | | CARLING | 06 | FULHAM | Home | 1 - 1 | Draw | | | PREM | 10 | Newcastle | Home | 2 - 2 | Draw | 10th | | PREM | 17 | Everton | Away | 2 - 2 | Draw | 10th | | CARLING | 20 | FULHAM | Away | 1 - 0 | Lost | | | FA CUP | 24 | SWANSEA CITY | Away | 1 - 2 | Won | | | PREM | 31 | Arsenal | Home | 1 - 2 | Lost | 11th | | February 2009 |
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| PREM | 07 | Tottenham | Home | 1 - 1 | Draw | 12th | | FA CUP | 14 | LIVERPOOL | Home | 1 - 2 | Lost | | | PREM | 21 | Sunderland | Away | 3 - 3 | Draw | 12th | | CHAMP | 24 | AZ ALKMAAR | Away | 0 - 1 | Won | | | PREM | 28 | WBA | Away | 1 - 2 | Won | 11th | | March 2009 |
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| PREM | 07 | Blackburn | Home | 0 - 0 | Draw | 11th | | CHAMP | 11 | AZ ALKMAAR | Home | 1 - 1 | Draw | Win 2-1 agg | | PREM | 14 | West Ham | Away | 3 - 1 | Lost | 12th | | PREM | 21 | Chelsea | Away | 1 - 0 | Lost | 13th | | PREM | 28 | Fulham | Home | 1 - 2 | Lost | 14th | | April 2009 |
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| PREM | 04 | Middlesbrough | Away | 4 - 2 | Lost | 15th | | CHAMP | 07 | BAYERN MUNICH | Home | 1 - 1 | Draw | | | PREM | 11 | Bolton | Home | 2 - 2 | Draw | 15th | | CHAMP | 15 | BAYERN MUNICH | Away | 1 - 1 | Draw | Win on pens | | PREM | 18 | Aston Villa | Away | 2 - 1 | Lost | 16th | | PREM | 25 | Stoke City | Home | 5 - 0 | Won | 14th | | CHAMP | 29 | Semi-1 REAL MADRID | Away | 2 - 1 | Lost | | | May 2009 |
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| PREM | 02 | Liverpool | Home | 3 - 3 | Draw | 14th | | CHAMP | 06 | Semi-2 REAL MADRID | Home | 1 - 0 | Won | Win away goals | | PREM | 09 | Manchester Utd | Away | 3 - 2 | Lost | 15th | | PREM | 16 | Manchester City | Away | 2 - 1 | Lost | 17th | | PREM | 23 | Portsmouth | Home | 2 - 1 | Won | 16th | | CHAMP | 27 | Final CHELSEA | Away | 1 - 2 | Won | CHAMPIONS! |
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