60. Gheorghe Popescu
Main Position: Central Defender Time With Spurs: 1994-1995 Having signed for
£2.9m from PSV Eindhoven, Gheorghe Popescu was part of a Tottenham side with an otherwise very poor defence that still managed to finish seventh in the 1994-95 Premier League season. He brought a touch of stability to the defence and class to the team, playing 23 times and scoring 3 goals before moving to Barcelona in 1995, where he replaced the legendary Dutchman Ronald Koeman and became club captain.
59. Justin Edinburgh
Main Position: Left Back. Time With Spurs: 1990-2000. Stalwart left back Edinburg was a mainstay in the Tottenham team for the best part of ten years, after joining from Southend United - initially on loan - before signing permanently. In his time at Spurs, Edinburgh won both the 1991 FA Cup final and the 1999 League Cup final (against Nottingham Forest and Leicester City respectively). Edinburgh made 278 appearances for Spurs - 215 of which were in the top flight (old First Division and Premier League) - scoring only once, before moving to Portsmouth for
£150,000 in the year 2000. Now 43 years old, he is the manager of Newport County.
58. Lewis Holtby
Main Position: Attacking Midfielder. Time With Spurs: 2013-Present. Yet to really make an impact at Spurs since his January 2013 move from Schalke, the German midfielder has still managed to show glimpses of the brilliance that made Spurs sign him in the first place. Spurs had agreed to sign Holtby at the end of his Schalke contract in the summer of 2013, but an injury crisis in the midfield led them to fork out
£1.25m to buy him out of his contract early. The current captain of the German U21 team and 3 time capped full international is seen as the long-term replacement for Luka Modric and, having seen some of his effortlessly, beautifully weighted passes, it's not difficult to see why. Having made 17 competitive appearances so far for the club, Holtby is yet to score. However, it is plain to see that he is a Lilywhites legend in the making.
57. Darren Bent
Main Position: Striker. Time With Spurs: 2007-2009. England striker Bent signed for Spurs from Charlton Athletic in 2007 for a then club record fee of
£16.5m. Scoring 18 times in 60 league appearances, Bent played 79 times in total for the club and scored 25 times. He was the club's top scorer in the 2008-2009 season with 17 goals in 43 games. Bent was an unused substitute in the 2008 League Cup final victory over Chelsea and moved to Sunderland a year later,
for £10m (which, conditionally, could have risen to the same fee that Tottenham paid for him), after openly criticising the club and the chairman. Now 29 years old and plying his trade at Aston Villa but could leave this season after a lack of first team games under Paul Lambert.
56. Clint Dempsey
Main Position: Striker. Time With Spurs: 2012-Present. American footballer-come-rapper Clint 'Deuce' Dempsey signed for Spurs from Fulham in August 2012 for a fee of around
£6m. The 30 year old has so far scored 12 goals in 43 appearances for the club, most notably the winner at Old Trafford against Manchester United in the Premier League and the last-gasp equaliser at White Hart Lane against Manchester United. Dempsey is the current captain of the United States national team and an acclaimed hip hop artist. His place at the club may come under threat should Spurs make any attacking signings this summer.