Shivam Pathak
Feb 27, 2026, 12:27 PM
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Friday's UEFA Champions League round of 16 draw saw Real Madrid paired with Manchester City once more.
Their first leg clash -- to be held on either March 10 or 11 -- will be their 15th UCL meeting, and will make it five consecutive years in which the two sides have met in a two-legged knockout tie.
Another mammoth collision is impending: between England's most successful side of the last decade and the 15-time European champions.
ESPN haven taken a look at the last four years the two have locked horns.
Real Madrid 3-1 Manchester City (6-5 agg.)
Semifinal second leg, 2021-22
DAX Images/BSR Agency/Getty Images
After a stunning 176 minutes of football, City looked all but through.
City led 1-0 on the night at the Bernabéu, and 5-3 on aggregate. Jack Grealish's shot from eight yards out from the byline -- to surely seal proceedings -- is cleared off the goal line by a desperate Ferland Mendy.
But with Real needing two to force extra time, Rodrygo struck just before stoppage time, before the Brazilian headed in an aggregate equaliser just 90 seconds later. Carlo Ancelotti, football's coolest customer, looked unfazed by his side's mind-boggling late show.
The job still wasn't done, though. Just three minutes into the extra 30, Karim Benzema was fouled in the area by Rúben Dias, and from the resulting penalty, the Frenchman completed the turnaround.
Real went onto the final vs. Liverpool, where they took home the trophy for the then-14th time.
Manchester City 4-0 Real Madrid (5-1 agg.)
Semifinal second leg, 2022-23
AP Photo/Jon Super
At long last, the following season provided City the statement night they craved over Real.
After a 1-1 draw in Spain, City dismantled the holders 4-0 at the Etihad, in one of the most complete performances of Pep Guardiola's tenure.
Bernardo Silva scored a first-half brace in just under 15 minutes to start things off, as City undeniably played Real off the park -- with greater possession, shots, and belief.
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A couple of misses from Erling Haaland did not even go down as a mark against City, as Manuel Akanji and Julián Álvarez wrapped things up in the second half, with Kevin De Bruyne on song as he knocked the ball around with incision, getting two assists for himself.
City carried their momentum in the final, with a 1-0 win over Inter Milan in Istanbul to take home their first-ever Champions League.
Real Madrid 3-3 Manchester City
Quarterfinal first leg, 2023-24
Manchester City's Phil Foden, left, battles with Vinicius of Real Madrid during their Champions League first leg. Getty Images
While a shootout the following week in Manchester decided who progressed, the first leg at the Bernabéu underlined why this meeting has become Europe's premier pairing.
The visitors struck after just two minutes with a clever low Bernardo Silva free-kick, which caught everyone unaware -- and once again sparked a rapid Real response.
Eduardo Camavinga's deflected effort got Real back level, before Vinícius Jr. played in Rodrygo two minutes later, who crept it past Stefan Ortega to cue bedlam.
The second half swung just as wildly -- Phil Foden rifled in from outside the area to get City on terms, before Josko Gvardiol's curled home to put his side back in the lead.
There was, of course, more -- as Federico Valverde's sweet volley sent both sides back to Manchester on parity.
While Real took the tie on penalties the following week, it encapsulated the mentality of two sides who just couldn't suppress the other.
Real Madrid 3-1 Manchester City (6-3 agg.)
Knockout playoff second leg, 2024-25
Clive Brunskill/Getty Images
While the first leg of this tie merits a mention with its cacophony of goals, the return leg in Madrid was where City were, remarkably, put to the sword.
The player responsible? Kylian Mbappé, of course.
A hat-trick from the Frenchman went unanswered, save a stoppage time consolation goal, as City were run ragged by one of the world's most frightening attackers.
The first, after just three minutes, was an audacious lob. The second capped off a slick Real move, with a feint off the left foot that left Gvardiol helpless on the ground.
His third saw him drill it low into the bottom corner from the edge of the area, just after the hour mark, to knock the wind out of City's sails.
The battle between Mbappé and Haaland was hotly anticipated over the two legs, and the man from Bondy came out on top -- and it may be the two marquee forwards who decide it when the two sides meet again in March.