The Reds have a steeped history with the Spanish giants in the past. The rivalry is Europe's past, present and now future.
1981 European cup final
The third European cup was won in Paris, France. It was the first ever meeting between the two sides in the biggest fixture of them all.
Bob Paisley became the first manager ever to win three European cups against Madrid who where appearing in their ninth final and had won six of them.
It was a shock to La casa Blanca to be defeated in Europe. They were the club who had dominated since its invention, but they had not been to a final in 15 years and the mutual feeling around the Bernabeu was one of excitement to be there against a Liverpool side that had been there and done it during the past five years.
The reds had finished fifth in the league that season, and needed to win the cup to ensure qualification for 1982.
An Alan Kennedy 82nd minute strike won the cup for Liverpool after a spell of pressure from Madrid. Vujadin Boškov's side were defeated and affected badly after losing La Liga in the final seconds, and now this; it was time for change.
In the Spanish capital, Marca's cover the next morning did not really agree with the approach taken, saying: "Wasted Final" and "Madrid sentenced themselves to defeat."
But Liverpool had landed the first blow on Madrid in this rivalry. The reds had made a huge statement defeating one of Europe's top dogs.
The Champions league always brought the best out of Liverpool under Rafa Benitez, and this two legged fixture was one of the highlights of that era.
After the Reds' first ever win at the Bernabeu, due to a late Yossi Benayoun header, Real Madrid came to Anfield for the second leg with a sense of shell shock but also optimism that they could still progress.
Instead the aggregate score ended Liverpool 5-0 Real Madrid. It was perhaps one of the most scintillating performances under Benitez. It summed up what that side was all about with Gerrard and Torres playing Madrid of the park.
Torres spearheaded the display and rubbed salt in the wounds of Madrid being from Atletico. His spin of Cannavaro was something to behold in two minutes and from there the all whites couldn't resist him.
It was also Steven Gerrard's 100th European appearance for the Reds and he capped it off in superb style with a penalty and then a half volley into the roof of the Kop's goal.
Liverpool were just to good in all aspects of the game for a Madrid side that was in transition but still full of stars.
Real bite back
During the most recent decade it has been Real who have gained the upper hand. The 0-3 win at Anfield in the group stage of 2014 was a display that signified just how far away Liverpool and Brendan Rodgers were from the elite.
Madrid cruised again in the Bernabeu this time with a 1-0 win. It proved to be the beginning of the end for Rodgers' time at the club, with a lot of fans feeling a sense of disbelief in the managers team selections. It was also proved as a catalyst moment for Steven Gerrard, who was remarkably left on the bench.
37 years after triumph in Paris the Reds yet again met the Galacticos this time in Kiev. After a rollercoaster of a European campaign seen Liverpool riding the crest of another unanticipated continental wave the final in Kiev was there to cap it off.
Real Madrid, on the other hand were fighting for their third Champions League in a row. It was the opposite of Paris where Liverpool had been dominating before hand, and Madrid had come out of nowhere.
It was heartbreak for the Reds in the worst way. The Salah injury made Liverpool stand still, and despite a great celebration for Sadio Mane's equaliser Loris Karius took centre stage and gave Madrid two goals.
La Blanca were yet again crowned Kings of Europe, but this game was harnessed a huge stepping stone for the Reds who learnt from their mistakes and won the Cup a year later. It was the start of something special for Jurgen Klopp's side.
Since that day in Kiev Madrid themselves have declined. The departure of Ronaldo was met with the ongoing disagreements with Bale, and their next already cooked 'Galactico' in Eden Hazard has been constantly injured.
But despite losing the title to Barcelona in 2019 they reclaimed it in 2020. However, this campaign has been vaguely similar to Liverpool's. Underwhelming and injury ridden. This two legged knockout tie is the hardest quarter final to predict, but Liverpool should certainly be confident that they can progress.