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#3 Dimitar Berbatov to Manchester United (£30.75M)
Dimitar Berbatov will go down as one of the classiest strikers in Premier League history. The Bulgarian joined Tottenham having already been a Champions League regular with Bayer Leverkusen. He brought immense technical quality and a clinical finishing ability to Tottenham in 2006.
The Bulgarian in his time at Spurs scored 28 times over two years. He was a fan favorite known for his elegance and calm finishing and went on to secure a PFA Player of the Year nomination in the 2006-07 season.
When Sir Alex Ferguson and Manchester United came calling, having lost Carlos Tevez to Manchester City, Tottenham were left with little choice but to sell Berbatov.
#2 Kyle Walker to Manchester City (£35M + 15M in add-ons)
Kyle Walker was signed by Tottenham at 19 years of age from his boyhood club Sheffield United. He was loaned out to a number of lower-table Premier League clubs such as Aston Villa and Queens Park Rangers.
A breakthrough 2011-12 season saw Walker not only break into the first team but win the coveted PFA Young Player of the Year award. He went on to make over 183 appearances in a Tottenham shirt. Manchester City launched an audacious 50 million pound bid for his services in 2017, making him the most expensive defender in Premier League history at the time.
Walker has justified his price tag and has gone on to become a mainstay in Pep Guardiola's defence. The former Tottenham man has been used in an inverted right-wing-back role vital to stop counter attacks and adding a passing option in midfield. Walker has won three Premier League crowns, an FA Cup and four League Cups with the Sky Blues.
#1 Gareth Bale to Real Madrid (£85M)
Perhaps Spurs's biggest-ever modern-day superstar, Welshman Gareth Bale grew from a quiet left-back arriving from Southampton to world-beater by the 2013-14 season. His rapid pace, which famously left Inter Milan's Maicon for dead in the Champions League, combined with his lethal left foot, made Bale one of the world's best left-footed attackers.
After finishing the 2011-12 and 2012-13 seasons as the PFA Player of the Year, Real Madrid came calling to find their newest "Galactico". Much like Luka Modric in the previous season, Spurs could offer little to convince Gareth Bale to stay on at Tottenham. They instead commenceds negation to land a sizable transfer fee for the superstar, amounting to a world record £85M.
With the transfer fee secured, Spurs went on a splurge in the market, signing the likes of Erik Lamela, Roberto Soldado and Christian Eriksen. All three players have gone on to have varying degrees of success with the London club. Gareth Bale surprisingly made a return on loan to Tottenham in the 2020-21 season after falling out of favour with Real Madrid manager Zinedine Zidane.
