A Steven Gerrard wonder-strike earned Liverpool a point against Middlesbrough, but the 1-1 scoreline all but ended their hopes of finishing fourth and qualifying automatically for the Champions League.
The skipper's 30-yard half-volley brought the Reds level after a first-half strike from Szilard Nemeth had given the visitors a half-time lead.
But the Reds, despite a much improved second-half display, couldn't capitalise on Everton's loss at Fulham.
Reds boss Rafa Benitez named a strong line-up as the chase to catch Everton neared a climax. The Spaniard continued to prioritise the Premiership and resisted the temptation to rest many of his key players ahead of the Champions League semi-final second leg with Chelsea.
Gerrard, Jamie Carragher, Steve Finnan and John Arne Riise all started, while Sami Hyypia and Luis Garcia dropped to the bench along with the recovering Djibril Cisse and Didi Hamann.
Boro manager Steve McClaren fielded an experienced Premiership team that included Jimmy Floyd Hasselbaink who was looking to improve on his impressive scoring record against the Reds. Skipper Gareth Southgate was fit to take his place after suffering a horrific head injury in midweek.
Harry Kewell made his first start since the Carling Cup final in March, in a desperate attempt to prove his form and fitness to Benitez ahead of Tuesday night's game.
It was a needless free-kick given away by Kewell which set in motion the chain of events that allowed Nemeth to break through the Liverpool defence and strike a low shot past Jerzy Dudek to give Boro the lead after just four minutes.
Kewell almost made amends by latching onto a Fernando Morientes flick-on, but knocked the ball too far in front allowing Brad Jones to easily gather.
In response to the goal, the Reds probed and postured but it was McClaren's crisp-passing visitors who looked more likely to extend their lead early on.
Liverpool finally steadied their ship and were almost level when Riise beat Jones to Antonio Nunez's teasing cross but the Norwegian's header floated just over the bar.
Riise looked to be the Reds' best chance of getting on level terms. A stinging 25-yard volley was too hot for Jones to handle, and almost ricocheted to Kewell in the 26th minute. Another shot by the Norwegian two minutes later whizzed pass Jones' left post.
Mauricio Pellegrino almost gifted the visitors a second goal ten minutes before the break when his deflection from a corner luckily fell into Dudek's arms, with Hasselbaink looking to pounce.
Pellegrino was removed at half-time, in favour of Luis Garcia, but in doing so Benitez removed his chief attacking threat by moving Riise to centre-half – for the first time in his Anfield career.
Garcia made an instant impact, rising higher than his slight figure would suggest to force Jones into a fine tip over from Finnan's cross.
But the impact made a minute later by Gerrard, had Anfield shaking to its rafters.
An incredible 30-yard half-volley sped past Jones to bring Liverpool level and the Kop to its feet. An effort like that on Wednesday would surely see Liverpool place a foot in the Champions League final.
Morientes, Garcia and Kewell all went close to grabbing a winner as Liverpool piled on the pressure, but they failed to fashion a clear chance in the closing stages.
MAN OF THE MATCH: Luis Garcia (Liverpool) – His introduction at half-time changed the game and the Spaniard's harrying and all-action display at least ensured the Reds did not crash to yet another Premiership defeat.