Liverpool are one of the great names in continental football, with five wins in the European Cup and Champions League, the most of any English teams.
However recent years have been harder at Anfield, with Liverpool failing to reach the knockout stages of the competition since 2009.
That will all change on Wednesday night when Jurgen Klopp’s team play the first leg of their round of 16 tie with Porto – although it will have to go some to match their last knockout game.
Liverpool travel to Porto ahead of their first Champions League knockout game since 2009
That game was an incredible 4-4 draw against Chelsea in their quarter final second leg
Liverpool lost the first leg 3-1 at Anfield, but were two-up at Stamford Bridge in half an hour
In the 2009 competition, the Reds were defeated at the quarter final stage by Chelsea, 7-5 on aggregate after a remarkable 4-4 draw in the second leg.
As Matt Lawton put it in his Sportsmail match report, ‘This was a Champions League tie played not by modern millionaire footballers but by maniacs, with what appeared to be a mutual desire to push the self-destruct button. A tie as memorable for the madness as the moments of pure brilliance.’
Chelsea looked to have finally secured safe passage through after Didier Drogba’s goal
Pepe Reina spilled Drogba’s flick in at his near post, one of a number of errors in the game
Chelsea begin their celebrations early after Alex thundered in a free-kick to make it 2-2
Frank Lampard’s goal for 3-2 was the signal for Rafa Benitez to take off Fernando Torres
The tie had appeared over after the first leg. Chelsea – reinvigorated under Guus Hiddink after Luis Felipe Scolari’s ill-fated spell in charge – had won 3-1 at Anfield.
However Liverpool were level in the tie after half an hour, thanks to Fabio Aurelio’s free kick, which bounced past Petr Cech as he organised his wall, and Xabi Alonso’s penalty, after the Spanish midfielder was fouled by Branislav Ivanovic.
With Stamford Bridge rocked and the impossible suddenly feasible, another goalkeeping error switched the momentum. Substitute Nicolas Anelka’s cross was flicked by Didier Drogba, however it should have been a regulation save for Pepe Reina. Instead, he spilled the ball over the line.
However Liverpool were not done – Lucas pulled one back with a deflected shot from distance
Dirk Kuyt scored another 60 seconds later, and suddenly Liverpool needed only one more goal
However a second goal from Lampard finally put Chelsea into the semi-finals after a classic
With Chelsea now in charge, they drew level on the night through a thunderous Alex free kick, and when Frank Lampard finished off a team move to make it 6-3 on aggregate with 15 minutes to play, the game was surely done.
Rafa Benitez certainly seemed to think so. The Liverpool manager had been tetchy all evening, at one point arguing with Hiddink to the extent that fourth official Alfonso Burrull had to intervene.
With ten minutes to go, Benitez decided to save his star player – Fernando Torres, then at the peak of his powers – for future games, replacing him with the less threatening figure of David Ngog.
Steven Gerrard was injured for the game, while John Terry also missed out with suspension
Benitez shakes hands with Chelsea interim manager Guus Hiddink after the game ended
Two minutes later, Benitez was left looking foolish as his side threatened to perform a comeback comparable to the one staged in Istanbul four years earlier.
Lucas’ shot flew past Cech via a heavy deflection off Michael Essien’s knee, before Dirk Kuyt brilliantly headed in Albert Riera’s cross. Steven Gerrard, sidelined with injury, was roaring his team mates on. John Terry, suspended for the game, was having kittens.
It was schoolyard football, and not only because it was now a case of next goal wins. That came from man-of-the-match Lampard with arguably the best of the evening, striking off Reina’s left hand post following a fine pass from Anelka.
Liverpool have struggled in Europe since: the best effort was reaching the Europa League final
So Liverpool exited the Champions League – and they haven’t had a huge impact on it since. Two group stage exits have been the sum of their contribution.
They have enjoyed greater success in the Europa League – reaching the final in 2016 – but failure to regularly finish in the top four of the Premier League has cost them dear.
Now, however, as they travel to Portugal, many Liverpool fans will feel they are back where they belong. If they can be half as entertaining as they were on their last foray, the neutrals will be pleased to see them too.