Tottenham Hotspur’s top 5 most expensive transfer sales of all time ranked.
Tottenham Hotspur are one of the famous Premier League clubs, but their status among the ‘Big Six’ in the country has been plagued by their inability to keep hold of their star players.
Former Spurs chairman Daniel Levy was a notorious negotiator, famed for his ability to drive a hard bargain and made a lot of money through player sales. However, following Levy’s departure as the executive chairman last September, the club has now got a new negotiating team led by CEO Vinai Venkatesham. And on Friday, the north Londoners confirmed the departure of Brennan Johnson to Crystal Palace.
Brennan Johnson has become Crystal Palace’s most expensive buy at £35 million, joining them on a four-year contract from Tottenham. After two-and-a-half seasons, the Spurs have decided to cut their losses on the 24-year-old, who became the hero in the Bilbao night in 2025 when he scored the winner in the Europa League final against Manchester United. The £35 million fee acquired makes the Wales international one of the most expensive sales in the Lilywhites’ history.
Without further ado, let us take a look at the top five sales in Tottenham’s history.
1. Gareth Bale – £85.9 million (to Real Madrid on September 1, 2013)
For the second time in as many years, Real Madrid raided Tottenham for Gareth Bale after poaching Luke Modric in 2012. In the process, the Welshman became the world’s most expensive player, with Real Madrid breaking their own transfer record, which had been set in 2009 when they signed Cristiano Ronaldo from Manchester United.
Gareth Bale had a trophy-laden time with Los Blancos, winning 17 trophies in total before hanging up his boots in 2023.
2. Harry Kane – £80.8 million (to Bayern Munich on August 12, 2023)
Bayern Munich shattered their club-transfer record when they bought Harry Kane in a £80.8 million deal from Tottenham in the summer of 2023. As a result, Kane became the second-most expensive sale in the history of Spurs.
Kane is the north London club’s highest goal-scorer with 280 strikes in 435 games. The England international has enjoyed a fruitful time at Bayern Munich and won his career’s first piece of silverware last season.
3. Kyle Walker – £44.8 million (to Manchester City on July 14, 2017)
After failing to sign Dani Alves, Manchester City boss Pep Guardiola decided to switch his attention to Kyle Walker. After tough negotiations, Man City paid £44.8 million to acquire Walker’s services from Tottenham.
At City, Walker went onto establish himself as arguably the best right-back in the Premier League. The England international made over 300 appearances for the Sky Blues, helping them win six Premier League titles, two FA Cups, four League Cups, the Champions League and the UEFA Super Cup. Currently, the veteran full-back plies his trade for Burnley.
4. Brennan Johnson – £35 million (to Crystal Palace on January 2, 2026)
Brennan Johnson officially completed his move to Crystal Palace on 2nd January, just seven months
on from scoring what was the most important Tottenham goal in nearly two decades. The Wales international struggled for game time since Thomas Frank was appointed as Tottenham head coach last summer, starting just six Premier League games.
Having departed for Palace now for £35 million, Johnson has become Tottenham’s fourth-highest sale in their history.
5. Dimitar Berbatov – £32.3 million (to Manchester United on September 1, 2008)
After joining from Bayer Leverkusen in 2006, Dimitar Berbatov spent just two seasons at Spurs as the allure of Man Utd proved too great to turn down after a summer of arduous negotiations in 2008. The Bulgarian netted 46 goals in 102 appearances across two campaigns for Tottenham.
Johnson’s departure to Palace has pushed Berbatov now to the fifth-highest sale in the north London club’s history.
