Revealed: Real Madrid defender that sent Cristiano Ronaldo ‘crazy’ & forced Portuguese superstar to swap wings

The Portuguese superstar completed a record-breaking transfer to Santiago Bernabeu in the summer of 2009. Versatile Netherlands international full-back Drenthe had already spent two seasons in Spain by that point, with regular game time taken in for the Blancos. The Dutchman never truly fulfilled his potential, but he did cause an illustrious colleague plenty of problems in training.

Van der Vaart, who made his own move to Madrid in 2008, has told Ziggo Sports of Drenthe’s duels with a five-time Ballon d’Or winner: “He liked to play against Cristiano Ronaldo in training. He found that to be a challenge. He wondered: 'Cristiano? Who is that?' Cristiano Ronaldo went crazy with him. He was fast, agile and technical. How was he going to pass you? At one point, Cristiano started running down the left wing because he no longer knew what to do with Drenthe.”

Ronaldo was more at home on the right flank during his time at Manchester United, but was moulded into a record-breaking striker by the Red Devils and Real. While he is considered to be an all-time great, Drenthe remains a tale of what could have been. Van der Vaart added on his fellow countryman: “What seems a shame to me, and I have also said it to him, is that Royston is the best left-back the Netherlands has ever had. If he had put aside his ego and his street football-style of playing, he would still have played as a left back for the Oranje until four years ago.”

Drenthe is now retired at the age of 36. He took in a nomadic career, with the five years he spent at Real Madrid broken up by loan spells at Hercules and Everton. He also spent time in England with Reading and Sheffield Wednesday and hung up his boots having represented 14 clubs and earning just one senior international cap for his country.