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It was meant to be a day of celebration for the Reds after Kenny Dalglish on Thursday signed a new three-year deal to become permanent manager of Liverpool for the second time.
But Tottenham didn't read the script with goals in either half from Rafael Van der Vaart and a controversial Luka Modric penalty sealing a win that took them back into fifth spot.
With one game remaining, Tottenham's fate is in their own hands after a result few saw coming as Liverpool's five-match unbeaten run came to an end.
Tottenham now know that a win on the final-day at home to relegation-threatened Birmingham will be enough to confirm their place in Europe for next season.
Dalglish has transformed the club's fortunes since taking over in January, with Liverpool's new owners having been fortunate to stumble upon a winning formula they could scarcely have imagined after replacing Roy Hodgson.
Yet Tottenham, who knew they had to win to keep alive their hopes of leapfrogging their Merseyside hosts, began like a side throwing caution to the wind.
As Liverpool struggled to get out the blocks, Tottenham surged into an early lead through van der Vaart in the ninth minute.
Anfield was silenced as Modric's corner was partially cleared and the Dutch midfielder, via a slight deflection off Glen Johnson, saw his 20-yards shot sail past Pepe Reina.
Liverpool's frustration was evident, with Luis Suarez even fortunate to escape with just a yellow card after striking Michael Dawson while the defender was on the floor.
Such was Liverpool's lethargy, it took until the 34th minute before the home side had their first serious effort on goal.
And then Jay Spearing's shot wide from 20 yards out summed up their showing.
Andy Carroll, back in the Liverpool team after injury, drew groans around the ground as he mistimed his header following Martin Skrtel's cross.
Liverpool were finding their feet though and in Suarez they had a player capable of turning the game.
The Uruguayan was a menace for the visitors in the first half and his free-kick on the stroke of halftime flew inches wide of Carlo Cudicini's right-hand post.
Van der Vaart's 14 goals following his arrival from Real Madrid have made him one of the most astute signings of the season.
But his injury woes show no sign of ending and he limped off moments after the restart.
Despite the loss of their playmaker, Tottenham increased their lead within minutes thanks to Modric's controversial penalty in the 56th minute.
John Flanagan appeared to go shoulder to shoulder with Steven Pienaar, but referee Howard Webb incensed the home fans by pointing to the spot, with Modric slotting home the penalty.
Liverpool, with so much at stake, were clearly rattled. Suarez blazed over the crossbar but the Reds were finding Ledley King, making his first appearance in six months due to his on-going knee problems, an increasing barrier.
But the home side lacked ideas to break down the north Londoners, with substitute Jonjo Shelvey coming closest to a breakthrough with a shot that flew inches wide late on.
