Ranking The 30 Tottenham Transfers in the Daniel Levy Era

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#5 Most Expensive: Darren Bent, Striker

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Transfer fee: £16.5 million
Former club: Charlton Athletic (Football League Championship)
Years with Spurs: July 1, 2007 — August 5, 2009
Stats: 79 appearances, 25 goals, 7 assists (in all competitions)

The first-ever club record transfer signing was striker Darren Bent from Championship side, Charlton Athletic. At the time of this signing, Bent had proven to many people that he was a great goalscorer with his two previous clubs Ipswich Town (129 appearances, 50 goals) and Charlton Athletic (76 appearances, 35 goals). And while Darren Bent did continue his streak of scoring plenty of goals with his third club, Tottenham, the English striker faced an uphill battle with Spurs throughout his two-year tenure.

During Martin Jol and Juande Ramos’ stints as manager, Darren Bent was more often than not, the fourth-choice striker behind Dimitar Berbatov, Robbie Keane and Jermaine Defoe. When Harry Redknapp took over as manager, with Keane and Defoe still on the squad and Peter Crouch available during the summer of 2009, Redknapp wanted to sign Crouch and bring him back home with Spurs. The eventual numbers game from the very beginning at the striker position, despite having a track record of scoring goals, was Darren Bent’s undoing unfortunately.

Next: Most Expensive: #4