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Tottenham Transfer History: 10 Worst Signings in North London


Tottenham transfer history: Since the inception of the Premier League, Tottenham Hotspur has experienced varying degrees of success, a journey that has often been defined by the players they’ve brought to White Hart Lane. When delving into the fascinating Tottenham transfer history, there have been a number of excellent acquisitions, but also some that fans would rather forget. Today, we delve into the top 10 worst contracts in the club’s history, reminding us all that the transfer window can be a tricky business.

Overview of Tottenham Hotspur club

Tottenham is a football club in London, the capital city of the United Kingdom of Great Britain and Northern Ireland.

Tottenham was founded in 1882. After first winning the FA Cup in 1901, they became the first club under the league division to do so since the Football League was founded in 1888. Tottenham was also the first club in the 20th century to win the League Cup and FA Cup double in the 1960-1961 season.

Spurs also won their first UEFA Cup in 1972, becoming the first British club to win two different European Cups. From 1950 to the end of the 2000s, the team always won at least one trophy a decade, equaling the record with Manchester United. In total, Tottenham Hotspur has won 2 national championships, 8 FA Cups, 4 League Cups, 7 Super Cups, 1 UEFA Cup Winners’ Cup, and 2 UEFA Cups. They are also runners-up in the 2018-19 UEFA Champions League. Spurs have a long history of confrontation with city side Arsenal, and the match between the two teams is named after the North London Derby.

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The 10 worst signings in Tottenham transfer history

In the Tottenham transfer news today, let’s take a look at the 10 worst signings ever in Tottenham.

Bongani Khumalo

tottenham transfer history

Bongani Khumalo arrived at Tottenham with only a £1.5 million contract, but he deserves to be considered the worst signing in Tottenham transfer history.

Khumalo is a defender who joined Tottenham in the January 2011 transfer window from South African side Supersport United. However, during his five-year stay at the London team, Khumalo did not have a single minute of play and was loaned out to Reading, Preston North End, Doncaster Rovers, Colchester United, and PAOK.


tottenham hotspur transfer history

Mido can be seen as the most unfortunate contract in Tottenham transfer history. He shone while playing here on loan from AS Roma but when bought permanently by Tottenham, he completely failed to express himself, scoring once in 12 games in the 2006/2007 season before being sold to Middlesbrough.

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Sergei Rebrov

Tottenham Transfer History

Coach George Graham decided to break the team’s transfer record to bring Rebrov back for a fee of £11 million (the previous record was £6 million for Les Ferdinand).

With the award of a five-year contract as a show of faith, things are going well for Rebrov, but the player has not lived up to expectations. At the age of 25 and short in stature, the Ukrainian player cannot compete with the big defenders in England. Just nine goals in Rebrov’s first season is not good enough for a player who has broken the Tottenham Hotspur transfer history.

Roberto Soldado

tottenham transfer history

Signed from Valencia after Spurs sold Bale, Soldado worked hard but never regained his former form. Two years in London with Soldado can only be summed up in two words “miserable” when he scored only 7 goals in the Premier League before escaping the hell of Tottenham to return to Spain. The Spanish striker’s goals tally in his first season was far from the return expected for his approx transfer fee. Currently, the Spaniard is still regularly shooting in the Granada shirt and wants to forget all memories of his time at Tottenham.

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Clinton N’Jie

Tottenham Transfer History

Clinton N’Jie is Tottenham’s next worst contract on this list. The 26-year-old joined Spurs from Lyon for a fee of £8.3m. The Cameroon star is completely out of tune with the home team. Not to mention, the knee injury also made the 9th striker sit out for a long time. Finally, after 14 appearances, Clinton N’Jie had to leave England to join Marseille.

Vincent Janssen

Tottenham Transfer History

Vincent Janssen is another worst signing in 10 years of Tottenham transfer history. The Dutch international joined Spurs from AZ Alkmaar for a fee of £17 million. Expected to succeed as a striker, but the number 9 striker reminded fans of two other failed deals, Grzegorz Rasiak, and Sergei Rebrov. The slide and decline did not stop, in the end, the 25-year-old striker had to leave the British representative in humiliation.

Federico Fazio

Tottenham Transfer History

Named next on this list of the worst signings in Tottenham’s history is Federico Fazio. The Argentinian international came to Tottenham from Sevilla for £8 million. The 32-year-old star got off to a good start but the Premier League environment was too harsh for him. The number 20 central defender has to fight hard to catch up in the top English league. In the end, injuries pushed Federico Fazio early to leave the North London representative.

Benjamin Stambouli

Tottenham Transfer History

Coach Mauricio Pochettino at the time wanted Morgan Schneiderlin but could not get him to leave Southampton. It is this that makes Tottenham frantically look for an alternative to fill the defensive midfielder position. Stambouli then had an impressive performance to help Montpellier win Ligue 1 and Spurs decided to spend £4.7 million to recruit the French player.


Tottenham Transfer History

Gilberto spent 4 years playing very successfully at Hertha Berlin (2004-2008) and convinced the Tottenham board to spend £1.9 million to bring him back to London in January 2008. The versatile Brazilian player, who can play well as a left-back, left-winger, and central midfielder, is expected to improve the strength of the Spurs’ squad to battle in the European Cup.


tottenham transfer history

With a salary of £55,000 a week and a Copa Libertadores and Club World Cup winner. Paulinho is expected to stand out and make a difference at Tottenham Hotspur. However, the dismissal of coach Villas-Boas in December 2013 made the Brazilian player lose his position. Even though he had started every match before. Gradually Paulinho became redundant at Tottenham and was sold to the Chinese team Guangzhou Evergrande for a fee of 10 million pounds.

Lessons from Tottenham Transfer History

The above examples from the Tottenham transfer history reveal the inherent risks in the football transfer market. Despite the detailed scouting and vast resources at the club’s disposal, errors in judgment can lead to underwhelming performances and wasted financial resources.

It’s not just the Premier League that sees such situations. Similar stories can be found in the transfer history of clubs like Man Utd, Manchester City, and Liverpool, and even abroad in clubs like Real Madrid. For all these teams, the bottom line is that it’s not just about the transfer fee, but the performances, the passion, and the ability to adapt to English football.

While some of these players might have performed well in their previous clubs or had impressive runs post their Spurs careers, their stints at Tottenham didn’t reflect their potential or justify their transfer fees.

These lessons should be well remembered as we approach the next season’s summer transfers. Whether you’re a fan eagerly awaiting Tottenham transfer news, or you’re just interested in the broader mechanics of football transfers, it’s essential to be mindful of the lessons from the past. The old saying rings true – those who do not learn from history are doomed to repeat it.


Exploring the world of football transfers, from the highs of successful signings to the lows of poor choices, is an exciting journey that fans all around the world love to follow. The Tottenham transfer history gives us an insightful overview of the risks and rewards involved in this process. As we await the next exciting transfer window, we’re reminded that, while not every player can make an instant impact, it’s the long-term influence and the players’ ability to adapt and grow that truly matters.

Thank you for joining us on this exploration of the Tottenham transfer history. We encourage you to stay connected with the world of football and keep an eye on Transfer In Football for the latest football transfer news and discussions.

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