Ranking The 30 Tottenham Transfers in the Daniel Levy Era

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#3 Best Youth Player: Aaron Lennon, Right midfielder

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Transfer fee: £1 million
Former club: Leeds United (Football League Championship)
Years with Spurs: July 1, 2005 — September 1, 2015
Stats: 364 appearances, 30 goals, 77 assists (in all competitions)

Before being phased out of Mauricio Pochettino’s team completely last season, Aaron Lennon had been the longest serving member of Spurs during the 21st century, since joining the club back in July 1, 2005. While Jermain Defoe spent 10 years donning the Lilywhites’ shirt, it was split up between two stints. The same for Robbie Keane who played for Tottenham in nine years.

As Tottenham’s mainstay at right midfield for six different managers and one caretaker manager, Lennon was a beloved player at White Hart Lane during his stay. He would become a part of a mid-table club upon joining and eventually leaving on good terms to see Tottenham fall short of two goals: a Champions League spot and lifting up the League Cup once again after the 2014-15 season.

Spurs are moving in the right direction under Mauricio Pochettino, but for 10 years, the player known as “Azza” was a big part of steering Tottenham to great heights. Two main highlights were being a part of 2008 League Cup winning team and a quarter-finalist in the Champions League.

Next: Best Youth Player: #2