10 Most Expensive Spurs Transfer Flops

4. Darren Bent (£16.5 Million)

Like Roman Pavlyuchenko, it could be said that Darren Bent was underutilised at Spurs, but it's hard to argue that his time at the club wasn't a success. Spurs signed Bent from Charlton Athletic in 2007 for a then club record fee of £16.5 million, but he never found his feet at White Hart Lane. He scored just eight goals in his first season and, although he was Tottenham€™s top scorer in the 2008-09 season with twelve goals, that would be his peak. He missed an open goal against Portsmouth, with Harry Redknapp saying €œmy missus could have scored that one€ and scored eighteen league goals in sixty appearances overall. He moved to Sunderland for £10 million in the summer of 2009, but not before criticising Spurs chairman Daniel Levy on Twitter, making his parting with the club even more bitter than his poor impact on the pitch already had.
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I'm a Tottenham Hotspur fan who loves comics and comic book movies.