10 most expensive signings by Tottenham Hotspur

#4 Darren Bent – €24.75 million

Darren Bent signed for Tottenham for a then club record 24.75 million euros in June 2007. He had earlier plied his trade in Charlton Athletic where he had been the highest scoring Englishman in the Premier League during the 2005-06 season (18 goals). Bent’s 13 goals in the 2006-07 season in a team doomed to relegation was a testament to his individual abilities.

The riches spent on him were not immediately repaid, though. He scored 8 goals in his first season at the club. His second season proved to be much more successful with 17 goals in total.

The bond, however, was not destined for long. After the additions of the likes of Defoe and Keane to Spurs’ attacking line, Bent found it best to move on. he completed a transfer to Sunderland in July 2009.