Liverpool limped out of the Champions League despite victory over Debrecen as Fiorentina beat Lyon in the other Group E match to seal a place in the last 
16.
Rafael Benitez's side knew only a win would give them any hope of reaching the knockout stages, and David Ngog clipped in early to secure the victory.
But it was a tame display from the Reds that typified their recent poor form.
Debrecen even had chances to draw, but in the end it mattered little and the Reds now drop into the Europa League.
It is the first time the 2005 champions have missed out on the knockout stages since the 2002-2003 season, but they can have little complaint.
The damage to their Champions League campaign had been done long before the game in Hungary, with defeats by Fiorentina and Lyon ensuring they needed a huge turnaround in the final two fixtures to make the last 16.
Even so, Liverpool's laboured victory over a sid
e lying sixth in the Hungarian league only served to underline just how out of sorts the Mersersiders are this season.
Coming into the match with only one win in their previous 10 matches, it was perhaps to be expected that they would be somewhat nervous.
They could hardly have hoped for a better start, as Fabio Aurelio's cross found Jamie Carragher at the back post, and the defender's header across goal was bundled in by Ngog from close range.
But despite almost completely dominating the ball, it did not settle the Reds as Benitez may have hoped and an oddly disjointed display rarely set the pulse racing.
Dirk Kuyt should have done better when he failed to make contact with a Gerrard cross and Ngog brought a flying save out of Vukasin Poleksic with a 20-yard curling snap-shot.
However, Liverpool's lack of conviction in the final third, combined with news of Juan Vargas's penalty goal for Fiorentina in the other Group E match which was announced over the stadium's public address system, allowed Debrecen to gradually abandon their defensive approach and grow in confidence as the match wore on.
The best of their chances fell to Gergely Rudolf, who headed Laszlo Bodnar's fabulous cross wide
when unmarked from eight yards out.
And only a smart block from Carragher prevented the same striker striding clear of the defence from Zoltan Szelesi's through-ball midway through the second half.
Liverpool were still dominating, and Gerrard forced a superb block by Norbert Meszaros when he was set clear by Lucas's pass.
But a distinct lack of zip and self belief betrayed their approach, and Rudolf forced a smart stop from Pepe Reina at the other end when his cross-come-shot flew towards the top corner, while Adamo Coulibaly almost snatched Debrecen's first ever Champions League point with a late snap-shot.
The game petered out, with Liverpool's eyes and ears immediately drawn to the result of Fiorentina's match against Lyon.
The news soon filtered through that the Italians had won 1-0, with many Reds players watching the final stages of the match on a television in the tunnel.
And the Merseysiders' mood will not be helped by the knowledge that the last time they dropped out of the Champions League after the group stages, they went on to finish fifth in the Premier League.
16.Rafael Benitez's side knew only a win would give them any hope of reaching the knockout stages, and David Ngog clipped in early to secure the victory.
But it was a tame display from the Reds that typified their recent poor form.
Debrecen even had chances to draw, but in the end it mattered little and the Reds now drop into the Europa League.
It is the first time the 2005 champions have missed out on the knockout stages since the 2002-2003 season, but they can have little complaint.
The damage to their Champions League campaign had been done long before the game in Hungary, with defeats by Fiorentina and Lyon ensuring they needed a huge turnaround in the final two fixtures to make the last 16.
Even so, Liverpool's laboured victory over a sid
e lying sixth in the Hungarian league only served to underline just how out of sorts the Mersersiders are this season.Coming into the match with only one win in their previous 10 matches, it was perhaps to be expected that they would be somewhat nervous.
They could hardly have hoped for a better start, as Fabio Aurelio's cross found Jamie Carragher at the back post, and the defender's header across goal was bundled in by Ngog from close range.
But despite almost completely dominating the ball, it did not settle the Reds as Benitez may have hoped and an oddly disjointed display rarely set the pulse racing.
Dirk Kuyt should have done better when he failed to make contact with a Gerrard cross and Ngog brought a flying save out of Vukasin Poleksic with a 20-yard curling snap-shot.
However, Liverpool's lack of conviction in the final third, combined with news of Juan Vargas's penalty goal for Fiorentina in the other Group E match which was announced over the stadium's public address system, allowed Debrecen to gradually abandon their defensive approach and grow in confidence as the match wore on.
The best of their chances fell to Gergely Rudolf, who headed Laszlo Bodnar's fabulous cross wide
when unmarked from eight yards out.And only a smart block from Carragher prevented the same striker striding clear of the defence from Zoltan Szelesi's through-ball midway through the second half.
Liverpool were still dominating, and Gerrard forced a superb block by Norbert Meszaros when he was set clear by Lucas's pass.
But a distinct lack of zip and self belief betrayed their approach, and Rudolf forced a smart stop from Pepe Reina at the other end when his cross-come-shot flew towards the top corner, while Adamo Coulibaly almost snatched Debrecen's first ever Champions League point with a late snap-shot.
The game petered out, with Liverpool's eyes and ears immediately drawn to the result of Fiorentina's match against Lyon.
The news soon filtered through that the Italians had won 1-0, with many Reds players watching the final stages of the match on a television in the tunnel.
And the Merseysiders' mood will not be helped by the knowledge that the last time they dropped out of the Champions League after the group stages, they went on to finish fifth in the Premier League.
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