Budapest - Liverpool's miserable season continued as they were knocked out of the Champions League at the group stage despite a 1-0 victory over Debrecen at the Ferenc Puskas Stadium here on Tuesday.
The five-time champions needed to win to stand any chance of progressing from Group E but Fiorentina's 1-0 victory at home to Lyon meant the Serie A side joined the French outfit in the knockout phase at Liverpool's expense.
David Ngog gave Liverpool an early lead with a neat close-range finish but Liverpool laboured thereafter and struggled to inject any kind of energy into their play after news of Fiorentina's goal filtered through.
The victory at least secures a berth in the Europa League but it will be scant consolation for a side whose last group-stage exit came in 2002-03.
Fernando Torres's absence has given Ngog his first real chance to shine in a Liverpool shirt and the Frenchman gave the visitors a nerve-settling early lead when he converted with a backheel after Fabio Aurelio's right-wing cross had been headed back across goal by Jamie Carragher.
Liverpool dominated possession despite a heavy, uneven surface but they received a reality shock mid-way through the first half when the stadium's tannoy announcer broadcast news of Fiorentina's opening goal.
Vukasin Poleksic twice denied Ngog, first comfortably and then with a spectacular flying save, before Gergely Rudolf spurned an excellent chance to equalise when he headed wide from eight yards as the hosts began to threaten.
Liverpool continued to dictate proceedings in the second period but they frequently ran into a wall of white shirts as the home side packed the midfield and dropped back to defend the edge of their penalty area.
Steven Gerrard twice came close to extending the away side's advantage, first seeing his shot superbly blocked by Norbert Meszaros and then forcing a good save from Poleksic with a side-footed effort.
The game in Florence hung heavy over the second half, with Lucas glancing a header wide from Dirk Kuyt's right-wing centre and Carragher also nodding off-target as Liverpool vainly sought to quicken the tempo.
Gerrard lashed over from 20 yards after a slaloming run from Daniel Agger, while Fabio Aurelio and Javier Mascherano both tested Poleksic, but there was precious little zip to the visitors' passing.
Benitez elected to withdraw Ngog for midfielder Yossi Benayoun with just over 10 minutes remaining and Liverpool's profligacy was almost punished moments later when Jose Reina had to palm over Rudolf's goalbound strike from wide on the right.
Reina then had to save from substitute Adamo Coulibaly with the last action of the game as Liverpool clung to a faint hope that was swiftly extinguished when the final whistle sounded in Tuscany.