A Tottenham flop XI from the past decade worth £106.2 million, including Barcelona, Milan and Arsenal alumni

Tottenham WHL

A look at some of Tottenham's less than stellar signings in the last 10 years…


Radek Cerny – loan (Slavia Prague) – January 2005 - May 2008

Arrived as back-up to England’s number one Paul Robinson and thrived in the role. The Czech ‘keeper managed just 16 appearances in his three years at the Lane and endured an almost two-year long stint without a single outing.


Alan Hutton - £9 million (Rangers) – January 2008 - August 2011

Arrived as a marauding, athletic right-back but left in the summer of 2011 – 51 games and 2 goals later – after being usurped by a more marauding and more athletic right-back in the shape of Kyle Walker.

Ricardo Rocha - £3.3 million (Benfica) – January 2007 - June 2009

The Portuguese central defender joined after impressive displays in Europe for Benfica, but what followed at Spurs was less than impressive and he was released two years later with a mere 14 appearances under his belt.

Vlad Chiriches - £8.5 million (Steaua Bucharest) – August 2013 -

1/7 of the ‘Magnificent Seven’ signed with the Gareth Bale windfall, Chriches arrived to much excitement. The Beckenbauer of Bucharest, he even had bicycle kicks in his Youtube highlights. Unfortunately, he wasn’t great at defending and should be heading off this summer, provided there are any takers.


David Bentley - £15 million (Blackburn) –July 2008 – June 2013

Lauded as the new David Beckham, the former Arsenal man promptly failed to deliver, but his 40-yard strike at the Emirates has ensured him of a place in every Spurs fans' heart.

Paulinho - £16 million (Corinthians) – July 2013- June 2015

The Brazilian Frank Lampard turned out to be a poor man’s Jermaine Jenas and took his career to soaring new heights last month when he completed his move to China’s Guangzhou Evergrande.

Kevin Prince Boateng - £5.4 million (Hertha Berlin) – July 2007 – August 2009

A hot prospect in German football upon his arrival, KPB waited until his Spurs career was well and truly over before deciding to be a very good footballer, and went on to enjoy three successful years at Milan.

Gilberto – £2 million (Hertha Berlin) – January 2008 – July 2009

Spurs never learned from their previous dealings with Hertha and Gilberto’s career went much the same way as KPB – just without all that success afterwards.


Giovani Dos Santos – £4.7 million (Barcelona) – June 2008 – August 2012

A much-hyped Barca youth product, Dos Santos had a hint of the Andros Townsend about him, excellent on international duty but very much less so for club. Has since rebuilt his career in Spain.

Darren Bent - £16.5 million (Charlton Athletic) – June 2007 – August 2009

The infamous missed header against Portsmouth which Harry Redknapp reckoned his ‘missus could have scored’ will forever tarnish Darren Bent and many forget he finished the club’s top goalscorer in the 2008-09 season.

Roberto Soldado - £25.8 million (Valencia) – August 2013 –

It was the glamorous big-money move for a Spanish striker who was to be the man to fire Spurs back into the Champions League. What has followed has been intriguing, frustrating, depressing and tragic – in that order.

View the full team below:


Hutton           Rocha      Chiriches

Bentley            Paulinho       Boateng             Gilberto

Dos Santos

Soldado            Bent

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