From the dawn of the modern transfer era to the current market, Real Madrid has redefined what it means to invest in a player. The Top 10 Most Expensive Transfers in Real Madrid History1. This deal makes him the most expensive African player in history, surpassing Nicolas Pépé’s record fee to Arsenal. Diomande was a target for Paris Saint-Germain and Liverpool, but his dream move to Real Madrid was secured after PSG withdrew from negotiations. Cristiano Ronaldo (2009)Arguably the greatest player in Real Madrid history, Ronaldo broke the world record after his €94 million move from Manchester United to Real Madrid.