5 Tony Andreu (2015)
Given Alex Neil took over as City boss in early January after moving down from the Scottish top flight, he didn't have long to work with the transfer window.
And while almost everything he touched at City in those first six months turned to gold, his late £1m swoop for his Hamilton top scorer – and on a three and a half-year deal to boot – has offered almost nothing in return.
Andreu, currently on loan at Dundee United, still has another year left on his current deal.
4 Carl Robinson (2006)
Brought to the club initially on loan from Sunderland before completing a £50,000 move from the Stadium of Light. Joined the club at a time when morale was low following relegation and fans never took to his style of play. For many, he passed the ball sideways too often and lacked the pace to affect games.
3 Luke Chadwick (2007)
Later on from scoring that debut goal against Ipswich, Chadwick found himself flung into an advertising hoarding and picking up a truly nasty gash to his knee. He was out for four months – during which time he made his switch from Stoke permanent for £220,000 in January. He made just 17 more appearances for City before finally leaving in January 2009.
2 Keith Briggs (2003)
Relegated with Stockport but highly rated at Edgeley Park, Nigel Worthington signed the 21-year-old defender – or more worryingly titled, utility player – for £65,000.
But City fans never got to see much of him. City's promotion push left Briggs behind, and his contract was cancelled barely 18 months later.
1 Luciano Becchio (2013)
Luciano Becchio had been prolific over a number of seasons at Leeds – including the one he was halfway through.
So the logic went, Becchio would arrive ready to hit it off immediately but there was no sign of the prolific form when he arrived at Carrow, and therefore the biggest reason for his arrival disappeared.
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