Since 2012, City have become a force to be reckoned with and have made sure to rub shoulders with Europe's elite.
That year was the first they came across Real, who have grown to become very aware of the threat City possess - particularly with familiar enemy Pep Guardiola in the opposing dugout.
Real and City have squared off 10 times in competitive scenarios before the first leg, with most games serving up plenty of entertainment.
And ahead of Wednesday's Champions League quarter-final second leg - finely posied at 3-3 - here's a look back at every meeting between them prior to this season.
Real Madrid v Man City head-to-head
Real Madrid 3-2 Man City - September 18th, 2012
The first meeting between these two giants, which came in the Champions League group stage, would set the tone for the rivalry we see today.
City weren't the favourites in this one but they fought to grab two leads via Edin Dzeko and Aleksandar Kolarov while relying on some top goalkeeping by Joe Hart.
But it wasn't to be with Jose Mourinho's team fighting back late in the second half through Marcelo, Karim Benzema and Cristiano Ronaldo at the death.
Man City 1-1 Real Madrid - November 21st, 2012
City would get a second bite of the cherry in a much more even reverse fixture.
Benzema tallied in the first half but Real Madrid didn't have it all their own way as a second-half penalty from Sergio Aguero ensured the spoils were shared.
City would go on to exit the 2012/13 Champions League bottom of the group and winless, while Real would reach the semi-final mark before succumbing to a Jurgen Klopp-led Borussia Dortmund.
Man City 0-0 Real Madrid - April 26th, 2016
Over three years passed until City and Real Madrid met on the competitive stage, only this time it came on an even greater scale in the Champions League semi-finals in 2016.
Both sides were much closer in quality this time around and it showed as a goalless stalemate was played out in the first leg in Manchester.
To this date, it is the only goalless draw of the head-to-head so far.
Real Madrid 1-0 Man City - May 4th, 2016
There wasn't too much excitement in the second leg either, but Real Madrid came out the stronger of the two and allowed their greater experience to do the talking.
Real limited City to just four shots in the game and forced an own goal from Fernando to break the visitors' hearts and book themselves a spot in the final.
Zinedine Zidane's team went all the way in 2016 to win a record-extending 11th Champions League title, edging a nail-biting final over rivals Atletico Madrid on penalties.
Real Madrid 1-2 Man City - February 26th, 2020
Almost four years passed until both teams faced each other, this time in the Champions League last 16, and the gap somewhat allowed City to close in even further.
It was City and Guardiola's first significant victory over one of Europe's top dogs, with Gabriel Jesus and Kevin De Bruyne scoring in the second half to recover from falling behind to an Isco opener.
The win was City's first ever against Real Madrid.
Man City 2-1 Real Madrid - August 7th, 2020
The COVID-delayed second leg in Manchester was just as good for City as they stamped their authority on the tie with a top showing despite the tight scoreline.
Raheem Sterling got things going inside 10 minutes before Benzema, the constant thorn in the Cityzens' side, equalised to make the aggregate score 3-2.
City held their nerve, though, with Jesus tallying midway through the second half to see the hosts through to the quarter-finals.
Man City 4-3 Real Madrid - April 26th, 2022
Another Champions League semi-final match-up between these two and the first-leg result in Manchester is arguably the most entertaining game to date.
At points, it looked like City would run away with it having taken 2-0, 3-1 and 4-2 leads, but the ever-resilient Real kept their noses in it.
Benzema continued his excellent record against City by scoring twice, which included a cheeky panenka penalty to reduce the arrears to 4-3 ahead of the second leg.
Real Madrid 3-1 Man City - May 4th, 2022
If the first leg wasn't dramatic enough, observers wouldn't have been ready for what they were about to witness in the return fixture at the Bernabeu.
Carlo Ancelotti's team looked down and out when Riyad Mahrez extended the visitors' aggregate lead to 5-3 midway through the second half.
Real had no answers for the majority of the match until young substitute Rodrygo burst onto the stage by netting twice in the 90th minute to stun City and keep the hosts' campaign alive.
The Brazilian's surge forced extra time and a sense of inevitability was in the air that Real would go on to win the tie, which they did via their focal point in Benzema.
He was felled by a clumsy tackle by Ruben Dias and the onus was on him to convert, which he did to send his team through to the Paris finale.
Real Madrid 1-1 Man City - May 9th, 2023
Yet another semi-final meeting and this time the results of both legs would be part of a vital step in City's club history.
The first leg in Madrid was cagey but well poised with Vinicius Jr and De Bruyne scoring either side of half-time to ensure a draw.
It wasn't the most exhilarating of games the two have played out, but it set up a key showdown at the Etihad Stadium a week later.
Man City 4-0 Real Madrid - May 17th, 2023
After City's last-gasp pain against Real in 2022, it was their time to seize the moment a year later.
City battered the visitors essentially the whole 90 minutes in Manchester with Guardiola's men utterly dominant against one of their fellow European powerhouses.
Bernardo Silva hit two in the first half to get the hosts rolling before Manuel Akanji and Julian Alvarez completed the romp in the second half.
The result was part of City's eventual treble-winning season having seen off Inter Milan in the final in Istanbul.
