40. Chris Armstrong
Main Position: Striker. Time With Spurs: 1995-2002. In June of 1995, Chris Armstrong signed for Spurs from Crystal Palace for
£4.5m. He played 173 times for Spurs, scoring an impressive 62 goals, including 48 in the Premier League, and was an unused substitute in the 1999 League Cup final victory against Leicester City. Armstrong moved to Bolton Wanderers
for free in 2002, but only made one League Cup appearance for them before moving back to his first club Wrexham. Now 41, he has been retired since 2005.
39. Dean Richards
Main Position: Central Defender. Time With Spurs: 2001-2005 The late Dean Richards joined Spurs in 2001 from Southampton for a fee of
£8.1m. At the time, it was the biggest transfer fee ever paid for someone who had never played a full international match. Richards' time at Spurs was plagued with injuries, but he impressed nonetheless and was often touted for a full international call-up when he was on form. He made 81 appearances for the club, all of which were in the starting line-up, and he was a solid defender for them. In 2005, Richards was forced to retire from football due to dizzy spells and headaches, as doctors said it would be detrimental to his health to continue playing. He sadly died 6 years later on the 26th of February 2001, reportedly from a brain tumour, though the definite cause has never actually been publicly disclosed. Less than two weeks later, on the 6th of March 2011, two of his former clubs, Wolves and Tottenham, met in the Premier League. The match was designated as a tribute game and, as such, featured several official and media tributes to Richards' career and life. Joining the teams in the centre circle at Molineux Stadium for a minute's applause before kick-off were his widow Samantha and his two sons Rio and Jaden, as well as representatives from his four former clubs (Ledley King for Tottenham, Claus Lundekvam for Southampton, Matt Murray for Wolves and Mark Lawn for Bradford City), two of his former managers (Graham Taylor and Dave Jones) and two former team-mates (Don Goodman and James Beattie). The match finished 3-3. R.I.P Dean.
38. Brad Friedel
Main Position: Goalkeeper. Time With Spurs: 2011-Present. American shot-stopper Friedel signed for Spurs
for free following his contract at Aston Villa coming to an end in 2011. Upon signing for Spurs, he was in the middle of a record run of consecutive games in the Premier League which continued until the 7th of October 2012, when Andre Villas-Boas named him on the bench for a match against his former club Aston Villa (preferring new signing Hugo Lloris, whom Friedel had initially kept on the bench himself). The run spanned eight years, three different clubs and an astounding 310 league games. Friedel's arrival at Spurs coincided with an upturn in defensive form. Spurs had struggled to replace Paul Robinson, with Brazilian Heurelho Gomes proving too prone to mistakes, and Friedel brought much needed stability to the Spurs backline. He's made 58 appearances for the club in total, 49 of which were in the Premier League. Now 42 years of age, Friedel is still with Spurs and is the Premier League's oldest player. How much longer his Spurs career (and his career in general) will last is open to question.
37. Steffen Freund
Main Position: Central Midfielder. Time With Spurs: 1998-2003. Commanding German international midfielder Steffen Freund joined Spurs for
£750,000 following a successful spell with Borussia Dortmund which saw him win the Bundesliga twice with them, as well as the Champions League. Freund famously never scored a single goal for Spurs in 131 appearances (the fans would often shout "shoot" whenever he got the ball), he won the 1999 League Cup with the Lilywhites against Leicester City. He moved to Kaiserslautern on a
free transfer in 2003 and then back to England on loan with Leicester City. Now 43 years old, he is back with Tottenham Hotspur as Andre Villas-Boas' assistant manager.
36. Peter Crouch
Main Position: Striker. Time With Spurs: 1998-2000, 2009-2011. Beanpole England striker Peter Crouch has had two spells at White Hart Lane. 'Crouchy' had his first spell with the club as a youngster, joining from the Spurs academy, but didn't play a single game for the club. He was loaned out to non-league Dulwich Hamlet and Swedish side IFK Hässleholm before leaving the club on a permanent basis to sign for Queens Park Rangers. Crouch cost Rangers the princely sum of
£60,000. In his second spell, following stints with the likes of Aston Villa and Liverpool, Crouch rejoined Spurs from Portsmouth for
£9m and made 94 appearances, scoring 24 goals. It was Crouch's strike in a 1-0 victory at Manchester City that ensured Spurs qualified for their one and only Champions League campaign and for this he will always have a place in the White Hart Lane faithful's collective heart. He signed for Stoke City for
£12m in 2011.