The 10 Best and Worst Transfers in Tottenham Hotspur History

Jerrad Peters@@jerradpetersWorld Football Staff WriterJanuary 21, 2014

The 10 Best and Worst Transfers in Tottenham Hotspur History

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    For every Bale, a Bentley; for every Modric, a Murphy.

    Tottenham Hotspur’s transfer history is checkered to say the least—not because they haven’t acquired some wildly successful players, but because they’ve often paid premiums for some epic flops as well.

    Following is a look at the 10 best and 10 worst Tottenham transfers in the Premier League era.

Best Transfers – 10: Michael Dawson

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    The current Tottenham club captain arrived at White Hart Lane from Nottingham Forest in 2005 along with Andy Reid in a combined deal worth £8 million.

    But while Reid made only 27 appearances for the club in two seasons, Dawson is currently in his 10th campaign at the club and was part of the team that won the 2008 League Cup.

    He has so far been capped four times for England.

9: Darren Anderton

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    Darren Anderton came through the ranks at Portsmouth but was signed by Tottenham ahead of the Premier League’s inaugural season in 1992.

    Joining for £1.75 million, the talented attacker played 12 seasons at White Hart Lane, made 30 appearances for England and lifted the League Cup in 1999.

    He retired after scoring three goals in 21 matches for League Two Bournemouth in 2009.

8: David Ginola

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    David Ginola joined Spurs in 1997 for £2.5 million.

    A member of the 1999 League Cup-winning side, the flashy Frenchman thrilled White Hart Lane for three seasons before joining Aston Villa for £3 million in July 2000.

7: Dimitar Berbatov

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    Dimitar Berbatov had already established himself as a proven goalscorer at Bayer Leverkusen when he caught Spurs’ attention, which is why he commanded a transfer fee just under £11 million.

    But it was a price tag the Bulgarian would repay over two seasons at White Hart Lane in which he would score 46 times and help lead the club to the 2008 League Cup.

    The following summer, Spurs cashed in on Berbatov, selling him to Manchester United for £30.75 million.

6: Les Ferdinand

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    Les Ferdinand was a boyhood Spurs fan, and in 1997 he got the chance to wear the lilywhite shirt when he moved to White Hart Lane from Newcastle for £6 million.

    He was part of the side that won the 1999 League Cup and enjoyed his best season at Tottenham in 2001-02 when he bagged 15 goals in all competitions.

5: Jurgen Klinsmann

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    Jurgen Klinsmann’s Tottenham arrival was greeted skeptically in 1994 when he arrived from AS Monaco for £2 million, but quite quickly it was apparent the Germany international was on his way to becoming a club icon.

    Klinsmann played 65 matches for Spurs over two stints, scoring 39 goals in all competitions and helping the club avoid relegation in 1998.

4: Robbie Keane

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    For £7 million, Tottenham Hotspur signed a player who would become one of the most important strikers in the club’s modern history.

    Robbie Keane scored at least 10 goals per season six times for Spurs and eclipsed the 20-goal mark in both 2006-07 and 2007-08, and in the summer of 2008 he moved to Liverpool for just over £20 million.

    But after things didn’t work out for him at Anfield, the Republic of Ireland international was repatriated to White Hart Lane for £16 million.

3: Luka Modric

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    Luka Modric was already a bona-fide star for both Dinamo Zagreb and Croatia by the time he joined Spurs for a club record fee-equalling £16.5 million in 2008.

    The midfielder quickly became renowned for his accurate ball distribution and helped the club achieve Champions League qualification in 2010.

    In August 2012, Modric joined Real Madrid for £33 million, earning Spurs a substantial windfall.

2: Teddy Sheringham

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    One of the most revered goalscorers of the Premier League era, Teddy Sheringham joined Tottenham Hotspur at the outset of the English top flight’s debut season in a £2.1 million move from Nottingham Forest.

    His 21 goals that season would earn him the Golden Shoe, and he never scored fewer than 14 Premier League goals in a campaign until 1996-97.

    That summer he joined Manchester United for £3.5 million, but he would return to White Hart Lane in 2001 and score 26 goals in all competitions in his next two seasons.

1: Gareth Bale

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    It’s hard to believe there was a time when Spurs couldn’t win a match with Gareth Bale in the team.

    Acquired from Southampton for an initial £5 million in 2007, the Welshman made 24 Premier League appearances before finally being part of a winning side, but by the time Spurs were playing Champions League football in 2010-11, it was clear Bale was on his way to becoming a world-class talent.

    Last season, he scored 26 goals in all competitions for the club before joining Real Madrid on a world-record transfer fee of £85.3 million.

Worst Transfers – 10: Louis Saha

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    Louis Saha joined Tottenham Hotspur on a free transfer on the final day of the January 2012 transfer window, agreeing a six-month contract at White Hart Lane.

    His presence at the club was little more than a luxury, however, as he played parts of only 11 matches in all competitions until moving to Sunderland the following summer.

9: Gilberto

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    Gilberto da Silva Melo, known simply as “Gilberto,” moved to Spurs in 2008 from Hertha Berlin, where three years prior he had been named the Bundesliga’s best left-back.

    Another January signing, the Brazilian hardly repaid the more than £2 million the club spent on him by appearing in just seven matches over parts of two seasons before joining Cruzeiro in July 2009.

8: Ben Thatcher

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    Tottenham paid £5 million for Wimbledon left-back Ben Thatcher in 2000, although shortly after the transaction manager George Graham was sacked and the Wales international failed to catch the eye of incoming boss Glenn Hoddle.

    Thatcher never played more than 12 Premier League matches in any of his three seasons at White Hart Lane, and in 2003 he was sold to Leicester City for a paltry £300,000.

7: Bobby Zamora

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    Bobby Zamora would eventually establish himself as a Premier League regular at West Ham and Fulham, but during the 2003-04 season he could barely get a game at Tottenham.

    Spurs had signed Zamora for £1.5 million in the summer of 2003, but after making the move from Division 1 Brighton & Hove Albion, his previous success failed to carry over into the Premier League.

    He failed to score a single goal for Spurs in the English top flight, although the club was able to flip him to West Ham in the deal that brought Jermain Defoe to White Hart Lane.

6: Danny Murphy

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    On the final day of the January 2006 transfer window, Tottenham Hotspur managed to blow £2 million on Danny Murphy.

    The former Liverpool and Charlton midfielder would play a bit role in 10 Premier matches down the stretch for Spurs that season, but he managed just 12 appearances for the club in the whole of the 2006-07 campaign.

    Murphy joined Fulham the following August.

5: Kazuyuki Toda

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    Chalk this one down to bad scouting.

    Shortly after Kazuyuki Toda had put in a solid 2002 World Cup for co-hosts Japan, he was brought in to Tottenham Hotspur, where it became immediately apparent that the midfielder was never going to adapt to the English game.

    He played only four matches for Spurs before being moved to ADO Den Haag, and at 36 years of age he is still playing for Singapore-based Warriors FC.

4: Grzegorz Rasiak

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    Grzegorz Rasiak is also still playing—for Warta Poznan in his native Poland at the age of 35.

    But in 2005, the former Derby striker joined Tottenham Hotspur for £3 million before struggling to make the first team and being loaned to Southampton after just eight appearances for the London side.

    Spurs did, however, manage to recoup £2 million of Rasiak’s transfer fee when Southampton made his move permanent in 2006.

3: Helder Postiga

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    Tottenham paid £6.25 million for Porto striker Helder Postiga in 2003, and much like Rasiak, the Portugal international failed to break into the first team and managed just a single goal in his only season at the club.

    The following summer Postiga was returned to Porto in exchange for midfielder Pedro Mendes, who also played just one full season at White Hart Lane before joining Portsmouth in January 2006.

2: Stipe Pletikosa

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    In the summer of 2010, Tottenham signed goalkeeper Stipe Pletikosa—a former Croatian Footballer of the Year—on season’s-long loan from Spartak Moscow.

    It was an altogether wasteful transaction.

    Pletikosa’s only appearance for the club came in a League Cup defeat to Arsenal, and after rotting in the reserves for an entire campaign, he signed a two-year contract at FC Rostov.

1: David Bentley

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    Blackburn Rovers midfielder David Bentley had scored 14 and 12 goals, respectively, in the two seasons before he joined Tottenham Hotspur in 2008.

    Considered, at least at White Hart Lane, to be one of English football’s rising stars, he was acquired for a whopping £15 million and signed to a six-year contract.

    He proved an absolute bust.

    Bentley scored just three Premier League goals in parts of three seasons at Spurs before being loaned out to Birmingham City.