Gareth Bale — Tottenham to Real Madrid (2013) — €100 million

Gareth Bale's £85.3 million (€100 million) transfer from Tottenham Hotspur to Real Madrid in September 2013 was the world record fee at the time, surpassing Cristiano Ronaldo's 2009 record. He justified every penny in his first season, scoring in the Copa del Rey Final and the Champions League Final. He won four Champions League titles at Madrid but his relationship with the Spanish media deteriorated after he was photographed on the golf course during injuries, and the "Wales. Golf. Madrid. In that order" banner at Euro 2020 became iconic.