Tottenham's 10 biggest sales of all time

Cameron Smith

• 22 Sept 2024 15:53 BST
• 6 min read

Tottenham Hotspur are one of the biggest football clubs in England, but their status amongst the country’s elite has been plagued by the fact their best players are almost always sold on.

The north London club have not won the English top flight since 1961 and their League Cup triumph in 2007-08 is the only trophy they have won in over 30 years.

They have constantly been near the European places over the past decade, while Mauricio Pochettino even guided them to the Champions League final in 2018. However, Spurs have never been able to keep hold of their best players - a theme that continued with Harry Kane in 2023.

This approach has seen them generate some impressive profits, but has ensured that trophies have been hard to come by.

Below, FootballTransfers runs through Tottenham’s 10 biggest sales of all time.

10. Oliver Skipp – €23.5m (to Leicester, 2024

Oliver Skipp came through Tottenham's academy as a highly-touted youngster but, despite more than 100 appearances for the club in all competitions, the midfielder was never able to become a first team regular in North London.

The former England under-21 international's best moment came in February 2023 when he scored his one and only senior goal for Spurs in the London derby against rivals Chelsea.

Skipp left Tottenham for newly-promoted Premier League side Leicester in the summer of 2024 for €23.5m.

9. Robbie Keane - €24m (to Liverpool, 2008)

Robbie Keane had a journeyman career, but his six year stint at Tottenham between 2002 and 2008 was the longest single spell at one club during his entire playing career.

The Irishman netted 80 Premier League goals during his first stint at Spurs, which convinced Liverpool to splash €24m on him, despite signing Fernando Torres the year prior.

Keane scored just seven goals for the Reds in 2008-09, before they sold him back to Tottenham for just €16.7m in the winter window, only six months after signing him for €24m.

8. Christian Eriksen - €27m (to Inter, 2020)

Denmark international Christian Eriksen became a fan's favourite during his time at Tottenham, but he was sold to Serie A giants Inter in January 2020 with his Spurs contract set to expire in six months time.

As a result, it was incredible business for the north London club to convince Inter to splash so much money on Eriksen, who could’ve been purchased for free half a year later.

The Danish midfielder made his Inter debut the day after signing, but left the club in December 2021 after Serie A rules stated he wouldn’t be able to play following a cardiac arrest at Euro 2020.

7. Michael Carrick - €27.2m (to Man Utd, 2006)

Spurs’ best player was nabbed by Sir Alex Ferguson’s Manchester United side in 2006, with Michael Carrick saying goodbye to White Hart Lane and hello to Old Trafford.

Carrick had spent just two years at Spurs after joining from West Ham, but they managed to turn an impressive €23m profit on the English midfielder after a stellar spell in north London.

He won 18 trophies at Old Trafford, before retiring in 2018.

6. Steven Bergwijn - €31.3m (to Ajax, 2022)

Steven Bergwijn enjoyed a dream Tottenham debut when he scored a stunning volley against Manchester City to help Jose Mourinho to a 2-0 win over his arch-nemesis Pep Guardiola.

Having arrived from PSV for €30m, much was expected of the Dutchman, but he was unable to become a regular at Spurs and was ultimately utilised as a bench option thanks to the presence of Heung-min Son and Dejan Kulusevski.

Incredibly, Spurs sold him back to the Eredivisie for €31.3m, claiming a nice €1.3m profit on the Dutch forward.

5. Luka Modric - €35m (to Real Madrid, 2012)

Luka Modric had been linked with a Spurs exit for several years before he finally left the club to join Real Madrid in 2012.

The Croatian was heavily pursued by Chelsea under Carlo Ancelotti, while Man Utd also held significant interest in him, but Daniel Levy refused to sell.

His move to Real Madrid even looked in doubt, but Jose Mourinho persisted and managed to seal a deal to bring the midfielder to Spain.

Modric was voted as La Liga’s worst signing after his first year at Real Madrid, but he answered back emphatically and has won the Champions League on five occasions.

4. Dimitar Berbatov - €38m (to Man Utd, 2008)

Two years after losing Carrick to Sir Alex Ferguson’s Man Utd, the same thing happened with Dimitar Berbatov.

The Bulgarian had spent five years at Bayer Leverkusen before joining Spurs in 2006, but he lasted just two seasons in north London as the allure of Man Utd proved too great.

Berbatov left Spurs having scored 46 goals and assisted a further 29 in just 106 appearances for the club, and he became a fan favourite at Old Trafford.

3. Kyle Walker - €52.7m (to Man City, 2017)

One of the first key signings of the Pep Guardiola era at Manchester City was the addition of Kyle Walker.

He had amassed over 200 games for Spurs after joining from boyhood club Sheffield United in 2009, and his pace and ability on the ball immediately improved Guardiola’s side, helping them become the dominant force in the Premier League.

Walker helped the side win the treble in the 2022-23 season and has been a great servant for Man City. His transfer fee has proven to be a bargain, but it was still good money for Spurs.

2. Harry Kane - €95m (to Bayern Munich, 2023)

Harry Kane smashed the Bayern Munich club transfer record in the summer of 2023 as he left Tottenham for an initial €95m.

In the process, Kane became the second-most expensive sale in the history of Spurs.

Kane was signed as the belated replacement for Robert Lewandowski, one year after the Bayern legend had left to join Barcelona.

The England international is the highest goal-scorer in the history of Tottenham, scoring an incredible 280 goals in 435 games. However, he never managed to win a trophy and that was a big reason in his decision to leave.

1. Gareth Bale - €101m (Real Madrid, 2013)

For the second time in as many years, Real Madrid raided Tottenham, with Gareth Bale following Modric to the Santiago Bernabeu.

In the process, the Welshman became the world’s most expensive player, with Los Blancos breaking their own record, which had been set via Cristiano Ronaldo’s move from Man Utd in 2008.

Bale arrived in Madrid after scoring 21 goals and providing eight assists in his final Premier League season. That form saw him win both the PFA Young Player of the Year award and the PFA Player of the Year award in 2013.

The former Spurs man won 17 trophies at Real Madrid before retiring in 2023 after a six-month spell at LAFC.

The 10 biggest Tottenham sales of all time