On one transfer deadline day, Manchester City pulled off one of the biggest transfer coups in their history - but it all ended in tears
07:00, 02 Feb 2026
Robinho at Man City
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Robinho's Man City career was a disappointment (Image: Getty)
One signing, above all others, is widely regarded as the spark that ignited the most successful era in Manchester City's history.
Over the past decade and a half, City have amassed an extraordinary haul: eight Premier League titles, three FA Cups, six League Cups and, at last, the Champions League in 2023. The story began on transfer deadline day in September 2008.
Abu Dhabi United Group, fronted by Emirati royal Sheikh Mansour, completed their transformative takeover of the club and immediately altered the trajectory of English football. Determined to announce themselves - and with time rapidly running out - City fired an audacious opening salvo by signing Brazilian superstar Robinho from Real Madrid for £32.5million.
Robinho and Mark Hughes
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City hijacked Chelsea's move for Robinho on transfer deadline day in September 2008(Image: Manchester City FC via Getty Images)
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The transfer sent shockwaves through the game. Not only had City landed one of the most highly rated young forwards in world football, they had done so by dramatically hijacking Chelsea's move for him.
The deal was thought to be done at Stamford Bridge. So confident were Chelsea that they had even begun selling Robinho shirts in their megastore - a move that allegedly angered Real Madrid enough for them to block the transfer, opening the door for the Citizens.
City's last-gasp intervention painted a stark and unsettling picture for their rivals. There was a new power emerging - and it had both ambition and financial muscle. What followed was a period of spending that would soon eclipse even Chelsea's early excesses under Roman Abramovich.
Robinho celebrates for Man City
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Robinho struggled to justify his price tag at City(Image: Getty)
It took four years for City to capture their first league title, but once the barrier was broken, the floodgates opened. Approaching 18 years on from the takeover, they stand as the dominant force in English football and a perennial heavyweight on the European stage.
Ironically, while Robinho's arrival may have been the first domino in a glittering, trophy-laden chain reaction, the former Brazil international himself played little role in City's on-pitch success.
Dramatically, he scored a goal on his debut against Chelsea, but Robinho was otherwise a total flop in Manchester. He stayed less than two years at the club before leaving for Milan where, a few years later, his career - and his life - would eventually come to a grinding halt.
Robinho
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The Brazilian was convicted of rape in 2017(Image: Getty Images)
The now 42-year-old was convicted of rape by an Italian court in 2017. Following years of appeals and failed extradition efforts by Italian authorities, Robinho, who denied the charges, was found guilty of taking part in the gang rape of a woman at a Milan nightclub in 2013.
He only started serving his nine-year sentence in Brazil in March 2024 and is currently incarcerated at Sao Paulo's notorious Tremembe prison complex, often labelled 'prison of the famous' because of its well-known inmates.
His crimes away from football have understandably eclipsed his achievements on the pitch, including the 18 months he spent at City. Nonetheless, Robinho's move to the Etihad remains one of the biggest transfer shocks in English football history.
Robinho of Manchester City jokes around with team mates during a training session, ahead of their UEFA Cup match against Aalborg, held at the Carrington Training Complex on March 11, 2009 in Manchester, England.
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Robinho's transfer sparked a revolution at City, but he played no part in their eventual success(Image: Getty)
At the time, rumours began circulating that the player thought he was joining Manchester United instead of their cross-town rivals, but Robinho quashed those rumours after signing on the dotted line.
"I knew that Manchester City is a very big club, there's a great team there already and this is an exciting project," he told City's website. "I liked the project, and when City made the offer to Real Madrid, I decided to come here. I liked the plans that Manchester City have and I want to succeed with them."
Speaking to the Mirror, he added: "I could understand why questions were asked about why I joined City last season because here was a club that had not celebrated any kind of success for many years.
Nigel de Jong, Carlos Tevez and Robinho at Man City
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Robinho left City before the trophy wins started pouring in (Image: Getty)
"It was said that I had come purely for financial reasons, that I had forgotten about my ambitions because of money. I said at the time that I signed because I had been sold a vision of Manchester City becoming a powerful club, not just in England, but throughout the rest of the world.
"Nobody was interested in listening to me a year ago but I think they will have to believe me when they see what is happening to City now. I think we are now on the brink of something very special. I want to win the championship this season. I think we can challenge for the title.
"Maybe it is still too soon and we have to have more time to develop as a team, but I do know I will be part of a team that will bring excitement to everyone.
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"Our attacking options are the best of any team. Signing Carlos Tevez, Roque Santa Cruz and Emmanuel Adebayor means I'll get even more opportunities to express myself because opponents will have other dangers to think about.
"Even our midfielders only know one way to play - to attack. Look at the threat we have in Shaun Wright-Phillips, Stephen Ireland and Martin Petrov. This is something very special."