Manchester City's reliance on free transfers has virtually vanished in recent years, but the club have made many over the years, with some working out well and others... not so much.

These are very worst of them from the past two decades, the ones that proved to not be worth the trouble, or the money.

Paul Dickov: It feels sacrilegious to put Dickov, a man who experienced two promotions and two relegations and played in three different divisions with City, at the top of this list. But it's his legendary status that made his second stint at the club so bitterly disappointing.

The Scottish striker returned to City in 2006, four years and one new stadium since he left Maine Road for Leicester. He wasn't the same player, however, and was stricken my multiple injuries in his first season back.

Dickov had signed a two-year deal, but spent the second-half of it on loan in the EFL Championship, first Crystal Palace and then Blackpool, in the 2007/08 campaign. He was released that summer without having scored a goal for City.

Steve McManaman: One could have forgiven Man City fans for being excited at the prospect of a two-time Champions League winner arriving to their club for absolutely nothing, but the Liverpudlian's spell at the club became notorious for non-footballing reasons.

Supporters became irked by his injury record and the amount of money he was earning for sitting on his backside - one fan wrote online that he was "too well off and too old to fight for his place" - but 'Macca' also found himself at the centre of a sordid story that became national news.

McManaman and City teammate Robbie Fowler enjoyed a wild night out in Colchester that ended with them in bed with "mother of three" Sharon Kelly. She sold her story to the News of the World, saying that the two players "think they're gods, but they're vultures".

David Seaman: Another England regular who was past his prime by the time he got to Manchester City, David Seaman joined the club after being released by Arsenal in 2003.

The legendary goalkeeper played 19 times in the league, conceding 24 goals and keeping the worst clean sheet percentage (21%) of his career, before being forced to retire due to injury at the age of 40.

David James was brought in as his replacement and fared somewhat better - when playing in goal rather than up front, at any rate.

Owen Hargreaves: The first-half of Owen Hargreaves' career was like a fairytale, leaving his native Canada for Europe at 17 years of age - despite only taking up football seriously at 15 - and going on to win multiple league titles and two Uefa Champions Leagues as well as being one of England's top performers in the mid-noughties.

Injuries ruined his final two years at Manchester United, but Hargreaves was determined to salvage his career, signing for City on a free in 2011.

The midfielder spent just 14 minutes on the pitch in the Premier League, however, and had to content himself with a view from the stands as the team went on to win the title on that famous day against QPR.

Sylvinho: The third two-time Champions League winner in our list, Sylvinho enjoyed a very successful spell at FC Barcelona in the noughties, which ended with a full 90-minute appearance in the 2-0 victory over Manchester United in the final in 2009.

The Brazilian left-back went from that historic moment to Man City, which would have garnered favour with the Blues faithful. However, Sylvinho only made six league starts for the Eastlands outfit in his only season at the club.

As a backup full-back to Wayne Bridge he was fine, but the then 36-year-old was unable to recreate his best form during the final season of his career.

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