In July 2009, Roger Federer won Wimbledon by defeating Andy Roddick in a five-set thriller. The match was the longest final in the Championship’s history at that time and marked the beginning of a glorious run for the Swiss. It was his 15th Grand Slam title and took him past Pete Sampras’ record of most Majors in the men’s singles category.

With 20 Grand Slams to his name as of today, Federer is still the man with the most singles Majors.

However, ten years after that epic win over Roddick, Federer’s chances of ending his career with the most number of Grand Slams took a mighty blow. And that setback came at the same venue – The All England Club. And ironically, it was in a match that is now the longest men’s singles final in Wimbledon history.

Had Federer defeated Novak Djokovic in the Wimbledon final this year, he would’ve taken his Grand Slam tally to 21 and built a considerable lead over his competitors. But the loss meant that Djokovic now has 16 Majors and is the closest he has ever been to Federer’s tally.

The Serb has often expressed his desire to finish with the most Grand Slam titles and he has long been regarded as someone who has the capability to overhaul Federer’s record.

As it turns out, though, the most pressing challenge for Federer as of now comes from the third member of this fascinating troika in men’s tennis – Rafael Nadal.

The Spaniard has an extremely physical style of play and has suffered numerous injuries through the course of his career. This compelled many to think that despite him being a true great of the sport and someone who has matched-up to Federer every step of the way, he wouldn’t be able to sustain and eventually overtake his great rival in terms of Grand Slams won.

But Nadal’s career has seen a tremendous upward swing over the past three seasons, in which he has bagged five Grand Slams. Now, with his latest triumph at Flushing Meadows, the Spaniard has reached 19 Majors and is within touching distance of Federer’s tally. Just like Djokovic, this is the closest he has ever come to the top of the pile.

Federer, at 38, doesn’t have age on his side as compared to Nadal and Djokovic, who are 33 and 32-year-old, respectively. The Swiss could have another period of resurgence, like he did in 2017 after returning from a six-month injury layoff, and add a Slam or two to his tally. But will that be enough to give him the record when the dust settles on the careers of these three legends?

Djokovic has several years of competitive tennis left in him and with his lofty fitness standards, it will take a brave person to bet against him winning more Majors. Nadal, too, is far from finished and will most-likely add to his total. Especially at the French Open, where he is still very much the undisputed king.

Sports is a funny business, though. Federer had won his 16th Grand Slam at the 2010 Australian Open and it seemed at that time that he wouldn’t take long to go past 20. But the Swiss could manage to win just one of the next 27 Majors. This isn’t to say that Nadal or Djokovic will face a similar low but again, anything is possible in the world of sports.

So, who do you think will finish with the most number of men’s singles Grand Slams – Roger Federer, Rafael Nadal or Novak Djokovic? Click here to join the debate.