The two most difficult matches to play in tennis are largely thought to be against Rafael Nadal on clay and Roger Federer on grass. The former won the French Open an unprecedented 14 times, while no player has won more titles at Wimbledon in the Open Era than Federer’s eight successes.

The three stars will be in the conversation for best men’s tennis player ever, but the All England Club can narrow its heroes down.

Federer and Nadal are both retired and although Djokovic reached the Wimbledon semi-finals he will have to roll back the years and produce an epic performance for the ages to win that coveted 25th grand slam and take sole possession of the record he shares with Margaret Court.

Rafael Nadal has opened up on his decision to skip Wimbledon 2025, with the tennis legend choosing to stay away from this year's tournament at the All England Club. The 39-year-old won the competition twice during his playing days as he established himself as a legend of the sport.

Carlos Alcaraz and Jannik Sinner are leaving the chasing pack in the dust.The pair have shared the last seven grand slam titles between them since the start of 2024, with Sinner prevailing in their Wimbledon final meeting one month on from losing their epic French Open showdown.

While Federer and Nadal were fiercely competitive with one another, Murray didn't manage to keep things quite as tight. The Brit had nine meetings with Nadal on clay over the year

SF lost to Rafael Nadal 6-3, 1-6, 1-4, retired