A brace from Luis Suarez in a 3-1 win over Zenit St Petersburg at Anfield was not enough to keep Liverpool in Europe as they went out on away goals.
Trailing 2-0 from the first leg, Liverpool threw everything at Zenit but were ultimately undone by an error from retiring defender Jamie Carragher, whose mis-kick allowed Hulk to grab an early away goal.
Needing to win 4-1, Liverpool dominated the game and got their hopes up when Suarez's double – including a wonderful free-kick – and a close-range finish from Joe Allen left them one goal from progress with half an hour remaining.
But, despite the hosts managing to carve out half a dozen chances, Luciano Spalletti’s side managed to hold on to move into the last 16 on the away goals rule.
It was a frantic episode from start to finish, with the hosts the conductors as they launched wave after wave of attacks at the Russian side, who looked punch-drunk at times.
However, they shot themselves in the foot early on when Carragher - making an English record 150th European appearance - completely mis-kicked his backpass, allowing Hulk to race clean through and slide the ball past Pepe Reina.
It would ultimately prove a sad end his continental football career, although his team-mates gave their all to try and give him another two legs in Europe, while he will be forgiven by his fans after winning two European titles in a long career.
Defensive partner Daniel Agger – returning to the XI in place of Martin Skrtel – dribbled the full length of the pitch before drawing a foul from Nicolas Lombaerts on the edge of the box.
Zenit spent more time and energy arguing the placement of the free-kick than sorting out their wall, Russia captain Igor Denisov earning a booking in the process.
That folly had a dual impact as Suarez was given more space to work with, while the terrible wall parted like Danny’s haircut to allow the shot to squirm into the bottom left.
Liverpool still needed three more goals without reply, and – after incessant pressure tempered by some shaky spells dealing with counter-attacks – they pulled another one back just before the break.
Jose Enrique, who had almost picked out Suarez on a couple of occasions, played a super one-two with Jordan Henderson before launching a cross into the six-yard box. Allen had continued a run from deep and, while his initial header was well saved by Vyacheslav Malafeev, the Wales midfielder rifled home the rebound for a 2-1 lead.
The hosts continued to bombard the visiting goal in the second half, roared on by the Kop.
It was manic at times, as Liverpool saw a decent penalty appeal waved away as the ball bounced into Tomas Hubocan’s arm, while Suarez’s shot was well saved by Malafeev.
Lucas almost sent Suarez clean through but the ball skimmed off his boot and into Malafeev’s arms.
Suarez had another chance soon after though, and he took it well. He had been fouled by Luis Neto around 30 yards out and after a discussion with Steven Gerrard he elected to shoot.
What followed was outstanding, as the ex-Ajax forward swung a fantastic swerving effort inside the top right corner with Malafeev flying at full stretch but nowhere near it.
With half an hour remaining and the momentum well behind them, a 2005-style comeback was on.
But, for all their possession and chances, Liverpool found Zenit and keeper Malafeev an immovable object.
Substitutes Oussama Assaidi and Jonjo Shelvey had impacts, the former lively and direct as he dovetailed with Suarez, the latter dynamic but thrashing a good chance wide after an error from Hubocan.
Gerrard had a flying volley saved in style by Malafeev, Agger put a header wide from a corner, while another Suarez free-kick was well saved by the visiting keeper.
There were a few half-chances for Zenit too, who occasionally exploited the holes at the back as Reina saved well from Hulk, who also had a long shot fly just wide.
There could be repercussions for Suarez, who evaded punishment after stamping on the back of Hubocan in the latter stages, while his team-mates seemed to seize up in injury time.
Zenit held on, Liverpool went out, and Swiss side Basel beckon for Spalletti’s side in a fortnight.