They wanted to make a statement in the 2008 transfer window and, on a frantic September deadline day, the Premier League club smashed their record transfer to pay Real Madrid £32.5million for Robinho.
While that might feel like a bargain nowadays, taking into consideration inflation, that fee would be more than £100m today.
The Real Madrid ace, though, didn't even seem to know where he was going and in the closing days, Chelsea and the Spanish giants agreed on a fee.
All looked in order as manager Luiz Felipe Scolari looked set to reunite with the Samba star he coached at when in charge of Brazil.
That was until Chelsea stores mistakenly began selling shirts with Robinho's name on them.
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At Real Madrid HQ, that did not go down well, and they immediately started working on terminating the deal
And so Chelsea accidentally sabotaged their own deal, which allowed City to steal in and land the forward.
"I wanted to go to Chelsea," Robinho told FourFourTwo in 2017, when he was playing for Brazilian side Atletico Mineiro.
"Scolari told me that I could make the difference for him in the team.
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"However, Real Madrid ended up badly with them, they didn't like the way that Chelsea sold shirts with my name on them before the deal was done.
"I am sure it was this that led to the negotiations to fail and it was a case of pride for Real Madrid.
"They were also reluctant to let me move to a club that was playing in the Champions League that season. Chelsea were, but City weren't."
Robinho's time at City was not as expected, despite arriving for a big fee, lasting just 18 months.
However, his career started with a bang when he put his new club a goal up against Chelsea, of all clubs, on his Premier League debut on 13 September 2008.
Scolari's men turned it around, though, as Ricardo Carvalho, Frank Lampard and Nicolas Anelka all got on the scoresheet to make it 3-1 and possibly plant a seed of doubt in Robinho's head.
While he might have finished his first year at the club as their top scoring player with 14 goals, the second season was plagued by injuries before falling down the pecking order.
"I moved to a great club and they welcomed me in the best way," he added. "I had one-and-a-half years of joy in Manchester, despite the city being a lot colder than Madrid!
"I don't regret leaving Madrid but I am sorry that it ended badly when I went."
He returned to his home country in January, signing for boyhood club Santos on loan before leaving the Premier League in the summer for AC Milan.
Further spells in Turkey, Brazil and China followed before a third return to Santos and retirement in 2020.
But it is his time in Italy that is continuing to haunt him.
Robinho, now 39, was sentenced to nine years in prison by an Italian court for rape.
In 2017, he was found guilty of taking part in a group sexual assault in Milan. Brazil does not extradite its citizens, though, and the former player has always denied the charges.
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In February, officials from Italy requested he serves his sentence in Brazil and a high court in the country will decide whether or not the court case will be translated from Italian to Portuguese and considered further by its own judiciary.