On September 1 2008, Manchester City were taken over by the Abhu Dhabi United group of investments, who subsequently made large amounts of funds available to overhaul the squad.
Here, we look at five of the worst signings since the takeover, including the likes of Kolo Toure, Emmanuel Adebayor & Roque Santa Cruz, but who takes the number one spot?
5. Kolo Toure
After spending seven years at the Emirates Stadium, the Ivorian was signed in 2009 by the Manchester club for £16 million.
In a hope to help make the club reach the top four, Toure was handed the captain's armband. Manchester City failed to do so as Spurs finished above them with a difference of just three points.
The following year, the armband was handed to Carlos Tevez, and he also failed a drugs test in March 2011 which resulted in a six-month ban.
Toure was released at the end of his contract in 2013 after being used as a squad player in his final season at the Etihad Stadium.
4. Emmanuel Adebayor
Another player brought in by Mark Hughes for a whopping £25 million from Arsenal.
The first player to score a hat-trick in a European competition for Manchester City fell down the pecking order after the arrival of Edin Dzeko, Mario Balotelli and Tevez.
The forward spent time at Real Madrid and Tottenham Hotspur on loan, before making a permanent move to the White Hart Lane outfit in 2012 for just £5 million.
3. Roque Santa Cruz
A player with so much promise completed his move to Manchester City for a fee believed to be around £17.5 million.
Santa Cruz had made only 19 league appearances during his first season at City and they finished the season in fifth position, where they qualified for the 2010/11 Europa League.
After making few appearances under former boss Mancini, the Paraguayan striker was loaned to Blackburn Rovers, Real Betis and Malaga before being released on a free this summer.
Signed for a British world record transfer of £32.5 million on deadline day from Real Madrid.
The lack of determination and skill for such a price tag was not something that would be accepted for a club which wanted Champions League football.
The Brazilian was loaned to Santos before permanently making a move to AC Milan.
Perhaps scored the most expensive goal for Manchester City at a staggering £18 million.
He was supposed to be a Brazilian magician when he arrived in 2008, but the affable striker only managed to stay at the club for half a season, in which he scored a solitary goal, before he was loaned out to Everton.
After being sent back to City a year later for breaching Everton's rules of conduct, he was shipped off to Galatasaray on the very same day.
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