It was the night of humiliation that ushered in Real Madrid's second Galactico era.
To the soundtrack of a fiercely passionate Anfield European night, the nine-time champions of Europe were put to the sword by an irresistible Liverpool attacking performance.
Fernando Torres, so long the symbol of Real's bitter rivals Atletico Madrid, revelled in opening the scoring before Steven Gerrard's double and a fourth from Andrea Dossena sent Real spinning out at the last-16 stage.
It's rare to see Real Madrid lose a match 4-0 and even rarer in the Champions League. But that was precisely what happened on March 10, 2009.
It was most likely the night that convinced Real to break the world transfer record a few months later to sign a certain Cristiano Ronaldo from Manchester United.
Fast-forward to the present and Real are preparing to once again line-up for a Champions League fixture without the talismanic Portuguese forward in their team.
It will feel strange when Real walk out at the Bernabeu to face Roma on Wednesday night that Ronaldo won't be there among their ranks, such was the transformative impact he had on their European fortunes.
Instead, Ronaldo will be playing about 350km away in Valencia, where Juventus begin their Champions League group stage. The post-Cristiano era for Real in Europe will begin.
The last time they played in the Champions League without him, on that night at Anfield, they were, in the words of the Daily Mail's Martin Samuel, 'pulverised.'
Samuel wrote: "Fittingly for the team nicknamed Los Merengues, Real Madrid were splattered and dispersed over a wide area of Anfield in the manner of an airy fairy dessert."
"One that had met a steamroller. Then another one. Then a herd of rampaging elephants. Driving more steamrollers."
"There was no contest here, no brave fightback, just the white flag of surrdener waved by a team who exist as a force in Europe in nothing but name."
How times have changed. Thanks in quite a large part to Ronaldo, Real Madrid are very much the pre-eminent force in European football once again.
They won the Champions League four times during his nine seasons with them, including in each of the last three. In that time, Ronaldo took personal charge of so many important games it's difficult to keep track.
Of course, Real were no slouches in that match in 2009. Their starting line-up at Anfield contained such stars as Arjen Robben, Gonzalo Higuain, Raul and Wesley Sneijder.
Their back line Sergio Ramos, Fabio Cannavaro, Pepe and Gabriel Heinze, with Iker Casillas in goal. It doesn't strike you as a team likely to receive a four-goal drubbing.
Yossi Benayoun's late goal had handed Rafa Benitez's Liverpool side a crucial advantage in the first leg, but nobody considered the tie done and dusted.
Yet Liverpool completely outclassed them from start to finish, with Torres doubling their aggregate advantage on 16 minutes when he turned home Dirk Kuyt's cross from close range.
Heinze was penalised for handball 12 minutes later, allowing Gerrard to score from the penalty spot.
And when Liverpool's captain slammed home Ryan Babel's cross two minutes into the second-half, it was truly game, set and match.
Dossena came off the bench to add a late fourth and only an exceptional performance by Casillas prevented Real suffering an even more embarrassing fate.
It was truly a season to forget for Real, who replaced manager Bernd Schuster with Juande Ramos midway through.
They finished nine points behind Pep Guardiola's Barcelona, who thumped them 6-2 in the Bernabeu en route to lifting the title and then went on to win the Champions League as well.
Yet this nadir proved a turning point for Real. That summer saw Ronaldo arrive from United for £80million, while the Spanish giants also signed Kaka, Xabi Alonso and Karim Benzema at enormous expense.
Ronaldo scored a staggering 105 goals in his 101 European matches for Real. And replacing that is not exactly going to be easy.