Success in Wimbledon betting is inevitably a requirement when ranking the greatest grass-court tennis players of all-time.

The Australian Open was played on grass until 1987, however, as was the US Open until 1974. The quantity of grass-court tournaments has decreased in recent decades, with just a five-week window in the middle of the European summer. 

Greatest Grass Court Tennis Players

  1. Roger Federer
  2. Martina Navratilova
  3. Novak Djokovic
  4. Serena Williams
  5. Pete Sampras

Lovers of the surface only have a short period to get stuck into online betting before the focus returns to the clay and hard courts. 

It’s never easy comparing generations, but we’ve given it a go to compile this list of the greatest grass-court tennis players of all-time.

Pete Sampras

With three consecutive titles between 1993 and 1995, and four straight between 1997 and 2000, Pete Sampras had an unprecedented period of dominance on the grass of the All England Club.

At the time of his retirement, Björn Borg was the only other man in the open era with more than three Wimbledon titles. 

Sampras, of course, has since been surpassed by Roger Federer. Novak Djokovic is currently level with the American on seven titles. 

When he hung up his racquet, Sampras had won the most Grand Slams in the Open Era, and had finished the most years as world number one. His 286 weeks as world number one was also an all-time record.

An attacking player throughout his career, Sampras had one of the greatest serves in the history of the sport, which set up his serve-and-volley game on grass courts.

From the baseline, he would invariably be aggressive, looking to put his opponents on the back foot early in rallies. A powerful second serve was a particularly dangerous weapon at Wimbledon.

Serena Williams

Martina Navratilova is the only woman with more Wimbledon singles titles in the Open Era.

Her winning percentage of 87.7% on grass is the second-highest in history to go along with seven Wimbledon titles and the Olympic gold on the grass of the All England Club at the 2012 Games. 

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There is a case to include Serena among the greatest women’s players ever on any surface. If it was put to a vote, most would consider her the GOAT. It’s a well-deserved honour for a player with a complete, dominant game. 

Power was the foundation of Serena’s brilliance, even if she mixed in plenty of precision and technical excellence.

The pace of grass courts only exaggerated the speed with which the ball flew off her racquet, whether unleashing a powerful serve or blowing opponents away from the baseline. 

Novak Djokovic

A seven-time Wimbledon champion, Novak Djokovic has the second-best grass-court winning percentage among all men’s players.

His game is a long way from the traditional serve-and-volley blueprint on grass, but Djokovic’s serve is incredibly accurate. It’s an area of his game which improved considerably through the first few years of his career. 

Widely considered the best returner of all-time, Djokovic is able to put pressure on opponents’ service games even on faster grass courts.

His knack for digging deepest for the most significant points and games has been evident on the grass of Wimbledon throughout his career, helping him on his way to seven singles titles.

Supreme flexibility and athleticism underpinned Djokovic’s game. There are no lost causes, and he has rarely been outfought in long rallies or fifth sets.

Martina Navratilova

With nine titles between 1978 and 1990, Martina Navratilova is the most successful singles player in Wimbledon history. Navratilova added a further 11 Wimbledon doubles titles, and claimed four Australian Open crowns on grass. 

Steffi Graf, Serena Williams, Chris Evert, and Margaret Court all had claims to be recognised as the greatest female grass-court player ever, but Navratilova’s sheer number of titles is impossible to overlook.

The accumulation of doubles titles illustrates her ability well past her physical peak.

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With an immensely accurate serve and a rounded, efficient game at the net, Navratilova was the archetypal serve-and-volley master on grass courts.

Her success on the surface is unlikely to ever be replicated, particularly with Wimbledon as the lone grass Slam.

Roger Federer 

With the best ever winning percentage on grass and a record eight Wimbledon singles titles, Roger Federer is the greatest grass-court player of all-time. His 192 wins on grass are also the most ever.

Effortlessly elegant, the Swiss phenomenon exploded onto the scene by beating Pete Sampras in five sets in 2000. Federer won the first of his eight All England Club titles in 2003, an honour he defended each year until an epic loss to Rafael Nadal in 2008.

Five more Wimbledon finals followed between 2012 and 2019 with three titles in that period. He also won Olympic gold at Wimbledon, beating Andy Murray in 2012.

While Federer spent much of his career at the baseline, he was just as comfortable coming to the net. He glided across the grass and had exemplary touch on the volley. He even mixed in an aggressive half-volley return against second serves.

From the baseline, both his forehand and backhand could deliver winners from anywhere on the court. 

Federer’s serve was not the most powerful on the tour, but he still got it into the high-130s, and opponents had a torrid time trying to read it. The type of serve was almost impossible to read from the ball toss or angle of his racquet. 

There was no debate over top spot in these rankings. Yes, Federer’s run of five straight titles came before Djokovic and Nadal were at their respective peaks, but he was the complete package on grass courts.

Anyone who watched him will fondly remember Federer for decades to come.


*Credit for the main photo belongs to Alamy*

Sam is a sports tipster, specialising in the Premier League and Champions League.

He covers most sports, including cricket and Formula One. Sam particularly enjoys those on the other side of the Atlantic Ocean – notably MLB and NBA.

Watching, writing and talking about sports betting takes up most of his time, whether that is for a day out at T20 Finals Day or a long night of basketball.

Having been writing for several years, Sam has been working with 888Sport since 2016, contributing multiple articles per week to the blog.