Tottenham supporters have enjoyed plenty of stars who have had the opportunity to call the club their home at some stage of their careers. The club have helped lay the groundwork for some of the Premier League’s best players.
However, with the lack of silverware, many of these key men have left in search of major trophies elsewhere.
These deals have broken the hearts of all their supporters, but they have been able to extract huge fees to build a squad once again of fierce fighters. Here from ReadTottenham is a list of Spurs’ top five sales.
5th – Dimitar Berbatov: Joins Manchester United for £30.75m – September 2008
The Bulgarian forward joined Spurs in 2006 from Bundesliga side Bayer Leverkusen. It took him time to adapt to the intensity of English football, but once he did, there was no stopping him.
In his final season at White Hart Lane, he scored an equaliser in the League Cup final against Chelsea, which they would win 2-1 in extra time, with 15 Premier League goals alongside it.
It wasn’t until deadline day that a deal was confirmed with the Red Devils. He went on to win two Premier Leagues, a Club World Cup and another League Cup under Sir Alex Ferguson.
4th – Brennan Johnson: Joins Crystal Palace for £35m – January 2026
The Welshmen had a tricky period ever since moving to North London from Nottingham Forest in 2023, whether it was the weight of expectations or just failing to fit into a new system.
However, he did end both full seasons as either top assister or top goalscorer, which included a goal in the Europa League final victory.
Fast forward to Thomas Frank’s reign, and he was primarily a backup to summer signing Mohammed Kudus. In a search for more regular football, the Eagles offered a way out, and he took it. Since moving, he’s featured in every single league game.
3rd – Kyle Walker: Joins Manchester City for £45 million – July 2017
After several loan moves to lower division sides, Walker finally got a chance to represent the Lilywhites in 2011, and he took it well. In 2012, he was named PFA Young Player of the Year, beating Sergio Aguero and Gareth Bale. He maintained his place in the team and quickly became one of the club’s best players.
His attacking prowess and ability to defend made him a leading candidate for some of Europe’s elite; that’s when Pep Guardiola pounced to bring him to City.
He’s won a plethora of titles, which include six Premier Leagues and a Champions League.
2nd – Harry Kane: Joins Bayern Munich for £82.3m – August 2023
One of, if not the best player to ever wear the White shirt of Spurs has one of the best goalscoring records in football history. Despite some loans, Kane scored 280 goals in 435 appearances for the Lilywhites, while also becoming the Premier League’s second-highest goal scorer.
After years of links to other clubs, he eventually joined the Bavarian giants, where his record is even better: 139 goals in 142 games.
Only one word to describe him. Ridiculous. He has since gone on to be crowned Bundesliga champion twice.
1st – Gareth Bale: Joins Real Madrid for £85m – September 2013
Bale began his career at White Hart Lane as a left-back, though he was quickly transitioned into a left winger, where he dazzled in the Premier League each week, becoming one of the world’s best players.
In 2012-13, he became the second player to win the PFA Player of the Year and PFA Young Player of the Year awards.
The only other player was Cristiano Ronaldo, and the Welshman would follow him to Real Madrid in 2013. His impact in Spain was gigantic, which included an overhead kick winning goal in the 2018 Champions League final, his fourth European Cup victory.
