Tottenham Hotspur have a world-class stadium which cost £1bn and they’ve also splashed the cash on several new signings over the years. However, their wait for a first trophy since 2008 goes on.
Spurs have also brought in big transfer fees for a plethora of stars, dealing with some of Europe’s biggest clubs in the process – but who is the club’s record departure?
Here is a look at Tottenham Hotspur’s most expensive sales in their history, with the help of news reports and Transfermarkt, with a detailed look at the top 10.
Rank
Player
Fee
Sold to
Year
Harry Kane
£86.4m
Bayern Munich
2023
Gareth Bale
£85.3m
Real Madrid
2013
Kyle Walker
£50m
Man City
2017
Dimitar Berbatov
£30.75m
Man Utd
2008
Luka Modric
£30m
Real Madrid
2012
Steven Bergwijn
£26m
Ajax
2022
Oliver Skipp
£25m
Leicester
2024
Kieran Trippier
£20m
Atletico Madrid
2019
Heung-min Son
£20m
LAFC
2025
Robbie Keane
£19m
Liverpool
2008
Michael Carrick
£18.6m
Man Utd
2006
Emerson Royal
£18m
AC Milan
2024
Kevin Wimmer
£18m
Stoke City
2017
Christian Eriksen
£16.9m
Inter
2020
Nabil Bentaleb
£16m
Schalke
2017
Toby Alderweireld
£13m
Al-Duhail
2021
Juan Foyth
£13m
Villarreal
2021
Ryan Mason
£13m
Hull City
2016
Nacer Chadli
£13m
West Brom
2016
Kyle Walker-Peters
£12m
Southampton
2020
Andros Townsend
£12m
Newcastle
2016
Peter Crouch
£12m
Stoke
2011
Pierre-Emile Hojbjerg
£12m
Marseille
2025
Here’s a detailed look at Spurs' top 10 sales… 10 Robbie Keane £19m to Liverpool, 2008
Robbie Keane was Spurs’ star player and captain back in 2008, so it was a real blow when Liverpool took him to Anfield for £19m. The transfer fee could have surpassed £20m, but we doubt the Irishman met the required add-ons.
Daniel Levy publicly spoke of their disappointment that Keane wanted a move away, but six months later, Keane was back at Tottenham on a permanent transfer after struggling to become a regular on Merseyside.
9 Heung-min Son £20m to LAFC, 2025
A Tottenham icon, Heung-min Son lifted Spurs’ first trophy in 17 years following the club’s Europa League triumph in 2025, but months later, the South Korea forward left north London for the MLS.
The attacker departed for LAFC in a deal worth £20m, with Son scoring 173 goals in 454 games for Spurs, proving to be worth every penny of the £22m Tottenham spent in 2015.
8 Kieran Trippier £20m to Atletico Madrid, 2019
Kieran Trippier’s final game for Tottenham came at Atletico Madrid’s Metropolitano Stadium in the 2019 Champions League final. It would end up being his new club home after Spurs sold him to Diego Simeone’s side for £20m that summer.
Trippier has since become a La Liga winner and returned to the Premier League with Newcastle United, where he helped them qualify for the Champions League.
7 Oliver Skipp £25m to Leicester City, 2024
After coming through the academy and making more than 100 first-team appearances, midfielder Oliver Skipp was sold by Spurs for a reported £25m in 2024.
Leicester City were happy to pay big for Skipp after winning promotion, with the player signing a five-year deal. For a player who didn’t quite reach his potential at Tottenham, it wasn’t the worst deal in the world.
6 Steven Bergwijn £26m to Ajax, 2022
Tottenham signed Steven Bergwijn in January 2020 in the hope that he’d further boost a very exciting attacking lineup under Jose Mourinho.
However, the Dutchman rarely started and wasn’t the attacking threat Spurs had invested in. Eight goals in 83 appearances isn’t exactly worth what they paid for him, so they did well to bring in a £26m fee in 2022.
5 Luka Modric £30m to Real Madrid, 2012
Luka Modric’s performances over a four-year period at White Hart Lane caught the eye of Real Madrid in 2012, who took the Croatia international to the Bernabeu in the summer of 2012 for £30m.
The midfielder went on to star in Spain and even won the Ballon d’Or in 2018, so the £30m fee is probably looked back on as a bargain for Madrid.
4 Dimitar Berbatov £30.75m to Man Utd, 2008
Stylish striker Dimitar Berbatov struck up a brilliant relationship with Robbie Keane in north London, with the former scoring 46 goals in 102 games.
Despite having Wayne Rooney, Carlos Tevez and Cristiano Ronaldo, Manchester United added Berbatov to their ranks in 2008, and he’d go on to win six honours with the Red Devils in four years following his £30.75m transfer from Spurs.
3 Kyle Walker £50m to Man City, 2017
Kyle Walker became the world’s most expensive defender when he joined Manchester City from Tottenham in 2017 for £50m, with the England international going on to win everything under Pep Guardiola at the Etihad.
Walker is arguably England’s greatest-ever right-back, but at the time, Tottenham had Kieran Trippier waiting in the wings, so were seemingly happy to cash in on him for such a large sum.
2 Gareth Bale £85.3m to Real Madrid, 2013
Gareth Bale followed Modric to Real Madrid in 2013 after starring in north London. The Wales international cost Real more than they had paid for Cristiano Ronaldo in 2009, with the transfer a world-record €100m (£85.3m) at the time.
Bale would go on to win 15 honours at the Bernabeu, including five Champions League titles. He scored 106 goals in 258 appearances in a Madrid shirt.
1 Harry Kane £86.4m to Bayern Munich, 2023
Topping the charts as Tottenham’s record departure is record goalscorer Harry Kane, who brought in £86.4m when he joined Bayern Munich in 2023.
The striker was linked with a Spurs exit on numerous occasions during his 13-year spell as a professional in north London, but it was the Bundesliga and Bayern that persuaded him to leave Tottenham. Kane, as expected, has gone on to continue to score for fun in Germany.