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Tottenham’s 10 most expensive sales & how they fared after leaving

Ben Stewart •

Tottenham have made some huge profits on players over the years and we couldn’t help but revisit their 10 most expensive sales of all time.

Harry Kane became the latest Tottenham superstar to leave the club and he will be looking to follow in the footsteps of some of Tottenham’s other record sales who have found success elsewhere.

Using figures from Transfermarkt, we’ve compiled Tottenham’s 10 most expensive sales and how they fared after leaving the club.

10. Kieran Trippier

The English full-back was looking for a fresh challenge in 2019 after four solid seasons in North London. Atletico Madrid snapped him up for £18.96million and he hasn’t looked back since.

Trippier had a superb experience in Spain and even got his hands on some silverware, winning the 2020–21 La Liga title. He’s now back in England and is smashing it for Eddie Howe’s Newcastle.

9. Robbie Keane

Liverpool came calling for the Irish forward in the summer of 2008, but it wasn’t long before he ended up back at Tottenham. The Reds decided to splash £20.68million on the forward, but he only lasted one year at Anfield.

Keane wasn’t quite as prolific during his second spell with Spurs and it wasn’t long until he then jetted off again, this time for LA Galaxy.

8. Christian Eriksen

The Danish playmaker was the orchestrator of Mauricio Pochettino’s Spurs side. By the time the January transfer window rolled around in 2020, he clearly wanted to experience a new challenge elsewhere.

Inter Milan snapped him up for £23.26million and he quickly bedded into Antonio Conte’s Inter side. Eriksen won the Serie A title in his first full season with the club and is now enjoying life at Old Trafford.

7. Michael Carrick

Manchester United wanted to sign Carrick to fill the void left by the departing Roy Keane and after a lengthy negotiating process, they managed to land a deal with Tottenham.

Signed for £23.44million, Carrick quickly established himself as a key component under Sir Alex Ferguson. With over 450 appearances for Manchester United and 17 trophies in the bag, it’s fair to say that this move was a resounding success for United.

After hanging up his boots, the former Spurs midfielder promptly went into management and has been doing a fine job with Middlesbrough since taking over.

6. Steven Bergwijn

The Dutch winger never really excelled in North London and Spurs did well to recoup their original transfer fee on the player. After three years with the club, Bergwijn departed in the summer of 2022 for £26.93million.

Since signing for Ajax, Bergwijn has looked right at home back in the Eredivisie. In his debut season for the Dutch club he scored 16 goals, which was double the amount he got in his three-year stay with Spurs.

5. Luka Modric

One of the defining transfers of the 21st Century. Real Madrid paid a mere £30.16million for the midfield maestro and the rest is history.

We still can’t believe he was initially voted as La Liga’s worst signing.

Real Madrid's Luka Modric during the Champions League semi against Borussia Dortmund at the Santiago Bernabeu, Madrid, 30 April 2013.

READ: Remembering when Luka Modric was voted La Liga’s worst signing

4. Dimitar Berbatov

Having scored 46 goals across two seasons in North London, plenty of clubs wanted to sign Berbatov in 2008. Tottenham accepted offers from Man City and Man Utd and the striker opted to join the red side of Manchester.

The Red Devils splashed £32.74million on the forward, which proved to be excellent value in the end. Berbatov scored 56 goals in four seasons with the club and got his hands on six trophies.

3. Kyle Walker

In many ways, Walker was one of the most transformative signings for Man City. He came in to replace the departing Pablo Zabaleta and City never looked back from that moment.

Walker won the Premier League title during his first season in Manchester and he has since gone on to win 14 trophies with the club. His £45.41million transfer fee was seen as expensive at the time, but to Pep Guardiola he has been worth every penny.

2. Harry Kane

Ange Postecoglou will be hard-pressed to find a replacement for Kane. The 30-year-old will go down as one of the Premier League’s greatest-ever strikers.

Following a lengthy negotiation process with Bayern Munich, Daniel Levy reluctantly accepted a £86.16million transfer fee, with potential add-ons to follow.

We’re sure he’ll go and smash it in the Bundesliga.

1. Gareth Bale

The Welsh winger became the most expensive player in the world when Real Madrid splashed £87million on the Tottenham star back in 2013.

Things might have ended on a sour note for Bale in Spain, but what a career he went on to have. Having scored over 100 goals for the Spanish outfit and producing countless clutch moments along the way, he’s forever etched into the history of Real Madrid.

Having won five Champions Leagues with Los Blancos, Bale has a genuine claim to be the greatest British footballer in history.

READ NEXT: Where are they now? Tottenham’s 7 Gareth Bale replacements from 2013

TRY A QUIZ: Can you name Tottenham’s top 30 goalscorers in the Premier League?

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