From Sergei Rebrov to Bongani Khumalo – Tottenham’s 10 biggest transfer flops since 2000

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Tottenham have pulled off some fantastic deals for players in recent years, but – like most clubs – they have suffered from some shocking trades, too.

Unfortunately, not every signing turns out to be successful which is sadly something clubs have to live with.

They may have bought Gareth Bale for £7m and sold him for a then world-record fee of £85million, but Spurs also splashed the cash on several players who turned out to be complete and utter disappointments.

With that in mind, let’s take a look at some terrible signings Tottenham have made in the Premier League era.

Sergei Rebrov (2000-2004)

Rebrov formed a formidable partnership with Ukraine legend Andriy Shevchenko whilst playing for Dynamo Kiev.

Yet while Shevchenko went onto win the Scudetto and Champions League, Rebrov struggled to adjust to his new surroundings. Bought for £11million in 2000, the striker managed just 10 goals in 59 Premier League appearances which is hardly something worth celebrating.

Milenko Acimovic (2002-2004)

The Slovenian was a signing after impressing in international tournaments at Euro 2000 and then the World Cup in 2002.

But much like other signings based on tournament football, he failed to live up to any hype. He made just 17 appearances for Spurs, failing to find the back of the net and will always be remembered for a shocking miss against Fulham, knocking the ball into the floor and over the bar from five yards out.

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Hossam Ghaly (2006-2009)

Acquired from Feyenoord in 2006, energetic Ghaly ruined his Tottenham reputation when he threw his shirt to the floor in protest after being substituted in a game against Blackburn Rovers.

He was later denied a squad number under former Spurs boss Juande Ramos and was forced to join Derby County on loan.

Kevin-Prince Boateng (2007-2009)

Boateng’s known for being a bit of a journeyman whilst his brother, Jerome, has become a club legend with Bundesliga giants, Bayern Munich.

Nevertheless, before Tottenham, he had only played for Hertha Berlin, and he promised to be an exciting talent for Spurs.

He cost the club more than £5m but only made 24 appearances in the 18 months he spent at White Hart Lane, before departing on loan to Borussia Dortmund in January 2009.

And to make matters worse, Boateng scored the winning goal for Portsmouth against Spurs in the 2009/2010 FA Cup Final.

Gilberto (2008-2009)

Left-back Gilberto joined from Hertha Berlin following four years in the Bundesliga and arrived with promise, especially after winning the Copa America with Brazil in 2007.

However, he went onto play just a handful of matches for the club and was substituted off at half-time in three of the seven games he’d started.

David Bentley (2008-2013)

Spurs once spent £17million on Bentley but in his five-year association with the club, he managed just 62 appearances.

After several loan spells in the Premier League, and bizarrely, Rostov in Russia, Bentley retired in 2013 after stating he’d fallen out of love with football.

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Bongani Khumalo (2011-2015)

Khumalo’s one of the worst signings in Spurs’ long history.

Despite a four-year stay with the club, the South African never played a single minute of competitive football for Tottenham.

Roberto Soldado (2013-2015)

Following the sale of Bale in summer 2013, Tottenham broke their transfer record three times. They firstly signed Paulinho for £17m in early July, before bringing in Soldado from Valencia for a fee of £26million, Erik Lamela later signed for £30million towards the end of that window.

Despite a fairly prolific record and reputation in Spain, Soldado struggled to score goals in England and was sold to Villarreal just two years later for less than half what Tottenham paid for him.

Clinton N’Jie (2015-2017)

Signed in 2015 for £8.3m, N’jie was expected to be a star for the future, but it never worked out that way.

Spurs eventually sold him to Marseille, and he went onto finish second in the 2018 Europa League.

In 2019, he moved to Dynamo Moscow on a four-year contract.

Vincent Janssen (2016-2019)

Janssen never lived up to his promise at Spurs after joining from Dutch side AZ for £17million in 2016.

He was eventually sold to Monterrey in Liga MX where he went onto win the 2019-20 league Championship despite finishing eighth in the regular season.

Source by Football London

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