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From Bongani Khumalo to Roberto Soldado: Tottenham’s 11 worst transfers of the Daniel Levy era

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As we are now in November it means it won’t be long at all before the transfer window reopens for business.

Tottenham did bring in four players ahead of the 2019/20 season and they are expected to be busy once again going on their dreadful recent form.

Mauricio Pochettino rarely strengthens in the winter transfer market but there’s a very good chance that will change come the turn of the year given he’s desperate to bring in some fresh faces.

 

Not all signings turn out to be major hits and Spurs have had their fair share of misses in the transfer market in the past.

Here we take a look at some of those since Daniel Levy became Spurs chairman back in 2001.

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Helder Postiga

The highly-rated attacker arrived in north London in 2003 after making quite an impression for Portuguese giants Porto during their 2002/03 treble-winning season.

While the goals flowed under Jose Mourinho as he hit 18 in all competitions before his move, he really struggled at White Hart Lane and was on his way back to his former club after only a year.

Postiga only scored one Premier League goal during his time at the club and it was definitely one to forget after so much hope back in 2003.

Helder Postiga only scored one Premier League goal for Spurs

Mbulelo Mabizela

Another player to join Postiga at the club ahead of the 2003/04 season was Mabizela.

The versatile player caught the eye while playing for Orlando Pirates against the Lilywhites in a pre-season friendly and Glenn Hoddle made a move to snap him up.

However, his time in the capital was short-lived as his contract was cancelled a year later due to a series of disciplinary problems.

 

Spurs fans will always have that thunderous strike against Leicester City to remember him by.

Timothee Atouba

Spurs had a new manager at the start of the 2004/05 campaign with Frenchman Jacques Santini swapping the national side for N17.

The new boss brought in a number of players during the summer including Atouba.

The Cameroon international did score a memorable goal at Newcastle United but that was the only highlight of his time at the club.

Timothee Atouba celebrates his goal at Newcastle
(Image: Ross Kinnaird/Getty Images)

He departed for German club Hamburg after just the one season at Spurs.

Grzegorz Rasiak

The less said about Rasiak’s time at White Hart Lane the better!

Arriving in England in 2004 after joining Championship side Derby County, Spurs decided to move for frontman a year later after his impressive form for the Rams.

He couldn’t replicate his performances in the capital and he was loaned out six months later as he sealed a loan move to Southampton, which became permanent in May 2006, after only eight appearances for the Lilywhites.

 

Gilberto

With one Gilberto impressing in north London at Arsenal, Spurs made their move to sign another Gilberto in 2008.

The left-back joined from Hertha Berlin in January 2008 and his performances left many supporters questioning how on earth he was a Brazilian international.

He only appeared in eight games for Tottenham before returning to his home country to join Cruzeiro.

David Bentley

A few months later and Tottenham spent big to complete the signing of David Bentley from Blackburn Rovers.

The England international really caught the eye for the Lancashire club and Spurs parted with £15million to sign a player who had been compared to David Beckham.

David Bentley up against former club Blackburn Rovers at White Hart Lane
(Image: Ryan Pierse/Getty Images)

Best remembered for scoring that stunning goal in the famous 4-4 draw at Arsenal and his infamous soaking of Harry Redknapp after clinching a top-four finish, the winger spent time on loan at Birmingham City, West Ham, FC Rostov and Blackburn before he finally departed Spurs in 2013 with only 62 appearances to his name.

Bongani Khumalo

Spurs dipped into the South African market once again in 2011 after signing Khumalo from SuperSport United after a successful trial at the club.

Amazingly the defender didn’t even play a single game for the club and ending up departing in 2015 after loan spells at Preston, Reading, PAOK, Doncaster Rovers and Colchester United.

He is now back at his former club in South Africa.

 

Ryan Nelsen

One year later and Nelsen arrived at the club on a free transfer from Blackburn.

A key part of the defence during his time at Ewood Park, the New Zealander’s time at the club would be short and sweet as he left for QPR a matter of months later.

Nelsen couldn’t replicate his form from his time at Lancashire in N17 and he left after only making eight appearances in all competitions.

Paulinho

Spurs had money to spend in the summer of 2013 after Gareth Bale finally completed his move to Real Madrid.

One of seven players brought in by Andre Villas-Boas as he looked to build a team capable of challenging for top honours, Paulinho flopped massively at Spurs despite so much optimism following his signing.

Paulinho had a couple of seasons at Spurs – not to great effect
(Image: Getty Images)

While he did score 10 goals in 67 appearances for the Lilywhites, he is probably best remembered by some fans for a truly dreadful attempt on goal away at Burnley.

Joining Chinese side Guangzhou Evergrande in 2015, Paulinho has since played for Barcelona and represented Brazil on a regular basis.

Roberto Soldado

Spurs spent another part of their money from the Bale sale on Spanish striker Soldado.

Scoring goals for fun in his three years at Valencia, it looked like the same would happen as he scored the winner from the penalty spot on his debut at Crystal Palace.

 

The goals unfortunately dried up and his time in the capital turned into a complete nightmare.

Soldado returned to Spain in 2015 as he joined Villarreal on a three-year contract.

Vincent Janssen

Spurs strengthened upfront once again in 2016 with the addition of Janssen for £17m.

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The Dutchman arrived at the club after a brilliant season at Eredivisie side AZ and everyone had their fingers crossed that he would transfer his form to the Premier League.

Behind Harry Kane in the pecking order at Spurs, Janssen’s chances in the first team were always going to be limited but he didn’t do anything near enough to suggest that he should play on a regular basis.

Despite Pochettino bringing him in from the cold last season in Kane’s absence, the striker moved on for good in the summer as he headed to Mexican side Monterrey.

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