The 10 most expensive Tottenham sales: Two Man Utd and Real Madrid deals behind Harry Kane

Despite being one of the Premier League’s ‘Big Six’ clubs, Tottenham Hotspur have often struggled to keep hold of their star players.

But Spurs chairman Daniel Levy is famed for his ability to drive a hard bargain and has made a lot of money through player sales.

We’ve taken a look at the 10 most expensive sales in Tottenham’s history and how those players fared after leaving north London.

Note: we’ve taken into account any potential add-ons when ranking the transfer fees.

10. Michael Carrick – £18.6m

Year: 2006

To: Manchester United

Tottenham appearances: 75

Tottenham goals: 2

Manchester United identified Carrick as a long-term replacement for Roy Keane and eventually agreed a £18.6million deal with Tottenham.

“I must say negotiations were very difficult and went on for ages,” Sir Alex Ferguson told MUTV. “I always remember I thought it was done and David Gill phoned me on the golf course to say they want more. Typical Daniel Levy!”

The deal represented a huge profit for Spurs, who signed the midfielder from West Ham United for just £2.75million in 2004.

But it also proved to be a great deal for United as he won five Premier League titles, two League Cups, an FA Cup, the Champions League, the Europa League and the FIFA World Club Cup during his 12 years at Old Trafford.

Michael Carrick is one of the most underrated players that the Premier League has ever seen, the fact that he only got 34 caps for England is criminal. 🤯

📽 @premierleaguepic.twitter.com/1s96KNqZyX

— Football Tekkers (@BallTekkers) January 13, 2023

9. Robbie Keane – £20.3m

Year: 2008

To: Liverpool

Tottenham appearances (first spell): 254

Tottenham goals (first spell): 107

After Liverpool declared a public interest in Keane, Levy made an official complaint to the Premier League. But the boyhood Liverpool fan handed in a transfer request and eventually got his dream move to Anfield.

“I have already made my opinion clear on the nature of this transaction,” Levy said after the £20.3million move was finalised.

“I don’t regard it as a transfer deal – that is something which happens between two clubs when they both agree to trade – this is very much an enforced sale for which we have agreed a sum of £19million as compensation plus a potential further £1.3million in additional compensation.”

The striker failed to justify that price tag, scoring seven goals in 28 appearances before rejoining Tottenham in January 2009 for a fee of £12million.

8. Kieran Trippier – £21.7m

Year: 2019

To: Atletico Madrid

Tottenham appearances: 114

Tottenham goals: 2

After starring in England’s run to the semi-finals of the 2018 World Cup, Trippier suffered a dip in form with Tottenham in 2018/19.

Mauricio Pochettino then decided to cash in on the England international, selling him to Atletico Madrid in a £21.7million deal.

He rediscovered his best form under Diego Simeone’s tutelage and played a key role in their La Liga title triumph in the 2020/21 season.

The right-back made 86 appearances for Atletico before returning to the Premier League with Newcastle United in January 2022.

7. Oliver Skipp – £25m

Year: 2024

To: Leicester City

Tottenham appearances: 106

Tottenham goals: 1

A Tottenham academy graduate, Skipp made over 100 appearances for his boyhood club but struggled to cement a consistent place in the starting XI.

He left in search of regular first-team football and joined Leicester City in a deal worth an initial £20million and £5million in add-ons.

But the midfielder also faced limited opportunities in his debut season at the King Power Stadium and was unable to prevent their relegation to the Championship.

6. Steven Bergwijn – £26.4m

Year: 2022

To: Ajax

Tottenham appearances: 83

Tottenham goals: 8

Bergwijn struggled for regular first-team action during his two-and-a-half years at Tottenham and was deemed surplus to requirements by Antonio Conte.

The PSV Eindhoven academy graduate controversially returned to the Netherlands and signed for their rivals Ajax in a £26.4million deal, making him the most expensive signing in Eredivisie history.

He registered 29 goals and 11 assists in 80 appearances during a two-year spell at the Johan Cruyff Arena before joining Saudi Pro League side Al Ittihad in 2024.

5. Luka Modric – £28.2m

Year: 2012

To: Real Madrid

Tottenham appearances: 160

Tottenham goals: 17

Having refused to sell Modric to Chelsea in 2011, Tottenham reluctantly accepted Real Madrid’s offer of £28.2million in the summer of 2012.

The Croatia international took a little while to settle in Madrid and was infamously voted as the worst signing of the season, alongside Barcelona’s Alex Song, by Spanish newspaper Marca in December 2012.

He turned things around and went on to win 28 trophies for the club, including four La Liga titles and a record-breaking six Champions Leagues.

The 39-year-old also won the Ballon d’Or award in 2018 and is widely regarded as one of the greatest midfielders of all time.

4. Dimitar Berbatov – £30.75m

Year: 2008

To: Manchester United

Tottenham appearances: 102

Tottenham goals: 46

Following a summer of protracted negotiations, Tottenham finally agreed to sell Berbatov to Manchester United on the final day of the 2008 transfer window.

“That whole experience was more painful than my hip replacement,” Ferguson said when reflecting on the £30.75million deal.

The former Bulgaria international scored 56 goals in 149 appearances in all competitions and claimed the Premier League Golden Boot in 2010/11.

His goals helped United win two Premier League titles, a League Cup and the Club World Cup, and he returned to London with Fulham in 2012.

This Dimitar Berbatov goal against Liverpool back in 2010 😱

(🎥 via @ManUtd) pic.twitter.com/TGbyPF8yt2

— B/R Football (@brfootball) January 17, 2021

3. Kyle Walker – £50m

Year: 2017

To: Manchester City

Tottenham appearances: 229

Tottenham goals: 4

After failing to sign Dani Alves in the summer of 2017, Manchester City manager Pep Guardiola then switched his attention to Walker.

City were initially reluctant to go above £40million but they agreed to pay Tottenham an initial £45million plus another £5million in bonuses.

The right-back has since made over 300 appearances for the club, helping them win six Premier League titles, two FA Cups, four League Cups, the Champions League and the UEFA Super Cup.

“We cannot understand the success we’ve had these years without Kyle,” Guardiola said. “It’s impossible. He arrived eight years ago with us and we start to win, win, win, win and he has been important for the national team and of course with our team.”

2. Gareth Bale – £85.3m

Year: 2012

To: Real Madrid

Tottenham appearances: 203

Tottenham goals: 55

Bale won the Premier League Player of the Year award in 2012/13 and his impressive performances attracted interest from Real Madrid.

While Levy insisted that the winger wasn’t for sale, Madrid came up with a then-world record transfer offer that was just too good to resist.

Bale enjoyed a trophy-laden career at the Bernabeu, winning five Champions Leagues, three La Liga titles, one Copa del Rey, one Spanish Super Cup, three UEFA Super Cups and three Club World Cups.

The former Wales international became a divisive figure among supporters but still scored 106 goals for the club, including a brace against Liverpool in the 2018 Champions League final.

🏴󠁧󠁢󠁷󠁬󠁳󠁿⚡️ 5 years ago today: Gareth Bale's goal vs Liverpool in the UCL final. Simply outstanding. pic.twitter.com/UgryprhR5t

— EuroFoot (@eurofootcom) May 26, 2023

1. Harry Kane – £100m

Year: 2023

To: Bayern Munich

Tottenham appearances: 435

Tottenham goals: 280

After becoming Tottenham Hotspur’s all-time top goalscorer in 2022/23, Kane then decided to leave the club in pursuit of silverware.

Despite the fact that he was entering the final year of his contract and would have been available for free in July 2024, Spurs still set a high asking price.

The striker eventually moved to Bayern Munich in a deal worth an initial £86.4million, with add-ons taking the price up to £100million.

He scored 36 goals during his debut campaign in the Bundesliga and won the Golden Shoe before firing Bayern to the league title in 2024/25.

READ MORE: The key contract details of every Tottenham first-team player: Expiry dates, weekly wages, agents…