10 most expensive signings by Tottenham Hotspur

#6 David Bentley – €22 million

David Bentley moved to Tottenham Hotspurs from Blackburn Rovers in 2008 summer. Bentley, with his 8 goals and 13 assists, was one of the reasons Blackburn had finished seventh in 2007-08 Premier League. His consistent performances also earned him a place in the England squad for the post-season friendlies.

The winger’s Tottenham career did not fly very high, though. After two disappointing seasons with the North London club, he was deemed surplus and was then loaned extensively. Bentley then had, mostly unsuccessful, loan spells at Birmingham City, West Ham United, FC Rostov and even his old club Blackburn Rovers.

Finally, after the expiry of his six-year contract, Bentley was released by the club in June 2013. He then retired from the sport citing lack of interest.