The 15 men to beat Novak Djokovic on grass – ft. Roger Federer and Rafael Nadal

Novak Djokovic has made the grass courts of Wimbledon his own in recent years.

The Serbian has won a staggering seven titles at the All England Club and also has a further title at Eastbourne in his collection, cementing his place as a great of the surface.

With doubts still circling over whether Djokovic will play at Wimbledon this summer, we look back at the exclusive club of players who can claim they have beaten him on grass.

1) Sebastien Grosjean – 2005 Wimbledon

Two-time Wimbledon semi-finalist and former world No 4 Grosjean was the first person to beat Djokovic on the surface when the future No 1 made his debut at SW19 in 2005.

The Serbian managed to make it through two rounds as an 18-year-old but was beaten in four sets by the ninth seed in round three 19 years ago.

2) Jan Hernych – 2006 ‘s-Hertogenbosch

Now established as one of the most talented rising stars on the ATP Tour, Djokovic was the eighth seed in ‘s-Hertogenbosch in 2006.

However, he was shocked in the round of 16 by Hernych, with the former world No 59 easing to a 6-2, 6-4 win on this occasion.

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3) Mario Ancic – 2006 Wimbledon

One of the greatest talents of the mid-2000s, Ancic – the seventh seed at Wimbledon in 2006 – edged past Djokovic in a thrilling round of 16 clash at the All England Club.

Djokovic pushed the seventh seed to the absolute limit, but the Croatian ultimately prevailed 6-4, 4-6, 4-6, 7-5, 6-3 to reach the quarter-final stage.

4) Arnaud Clement – 2007 Queen’s

Djokovic rarely played Wimbledon warm-up events throughout his career, but did so more often during the earlier parts of his career.

And he was handed a tough defeat against former Australian Open finalist Clement at Queen’s in 2007, with the Frenchman rallying from a set down in this round of 16 encounter.

5) Rafael Nadal – 2007 Wimbledon, 2008 Queen’s

Undoubtedly Djokovic’s greatest rival, Nadal was able to get two wins over the 24-time Slam winner on grass in the late 2000s, before the Serbian turned things around on the surface.

Nadal won their 2007 Wimbledon semi-final after Djokovic retired in the third set, before edging a tight Queen’s final between the two the following season.

6) Marat Safin – 2008 Wimbledon

Djokovic was a Grand Slam champion by Wimbledon in 2008, having won the Australian Open earlier that season.

And he was a significant favourite for his round two match against Safin, though the former world No 1 produced the form that took him to two major titles in a stunning straight-sets victory.

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7) Tommy Haas – 2009 Halle, 2009 Wimbledon

A former world No 2 and Olympic silver medallist, Haas beat Djokovic twice on the grass across the summer of 2009.

The German first beat Djokovic on home turf in Halle, prevailing in three sets to win the title, before winning in four sets when the two met in the last eight at the All England Club.

8) Xavier Malisse – 2010 Queen’s

Former SW19 semi-finalist Malisse rolled back the years to shock Djokovic at Queen’s 14 years ago.

The Belgian was a significant underdog against the second seed, but edged past the Serbian 6-3, 4-6, 6-2 to reach the last eight at the prestigious event.

9) Tomas Berdych – 2010 Wimbledon, 2017 Wimbledon

One of the cleanest ballstrikers of his generation, Berdych twice knocked the 24-time major winner out of Wimbledon.

The first such occasion was at the Championships in 2010, with the Czech producing a scintillating display in the last four, before Djokovic was forced to retire with injury in their 2017 quarter-final.

10) Roger Federer – 2012 Wimbledon

Djokovic generally had the edge against Federer in their grass-court meetings, but the Swiss prevailed when the two met at the All England Club in 2012.

World No 1 Djokovic was looking to defend the title after his maiden victory in 2011, but Federer produced some stellar tennis to prevail in their semi-final clash.

11) Andy Murray – 2012 Olympics, 2013 Wimbledon

Another frequent rival of Djokovic’s, two of Murray’s most significant career wins came over the Serbian across 2012 and 2013.

Murray beat Djokovic in the Olympic semi-final at London 2012 on his way to gold, before downing his nemesis once again to win the first of his two Wimbledon titles in 2013.

12) Juan Martin del Potro – 2012 Olympics

Djokovic was one of the favourites for Olympic gold at London 2012, but was ultimately unable to take home a medal.

Following his defeat to Murray, he then was beaten by former US Open winner del Potro in the bronze medal playoff.

13) Sam Querrey – 2016 Wimbledon

One of the biggest upsets in Wimbledon history, Djokovic was stunned by Querrey in four sets at the All England Club in 2012.

Djokovic was highly fancied to win a third straight title at SW19 and move one Slam closer to the calendar Grand Slam, but the American edged past the all-time great in a thrilling four-set battle.

14) Marin Cilic – 2018 Queen’s

Djokovic won the majority of his matches against Cilic, though the Croatian was able to beat the Serb in a high-quality Queen’s final six years ago.

The 24-time major champion held a match point in this contest, but Cilic battled back to prevail 5-7, 7-6(4), 6-3 to win his second Queen’s title.

15) Carlos Alcaraz – 2023 Wimbledon

After a hugely impressive four straight titles at the All England Club, Djokovic’s Wimbledon stranglehold was broken by Alcaraz in a dramatic five-set final a year ago.

It looked as if Djokovic could ease to victory after a dominant opening set, but Alcaraz rallied and claimed his first SW19 title with a 1-6, 7-6(6), 6-1, 3-6, 6-4 victory.

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