Grand Slam History: Most Winningest Tennis Players

The standard measure of the winningest men’s and women’s tennis players of all time focuses on the tally of Grand Slam title victories—the golden measure of a player’s success. Each of the four major tournaments—Australian Open (played on hard court surfaces in January), French Open (played on clay surfaces in May-June), Wimbledon (played on grass surfaces in July) and U.S. Open (played on hard court surfaces in August-September)—are considered Grand Slam events. Winning a Grand Slam title refers to winning any one of the four majors. The term ‘Grand Slam’ technically refers to winning all four majors in the same year, a feat achieved by only five singles players in history, with the most recent in 1988.

In this list, we explore the careers of the six players (three men and three women) with the most Grand Slam titles, celebrating their remarkable achievements and dominance in the sport. To put it into perspective, these are the only six singles players to crack 20+ Grand Slam tournament titles. On the men’s side, the next closest tally is Pete Sampras’ 14. 

T-1. Margaret Court – 24 Grand Slams

Australian tennis legend Margaret Court, whose career spanned from the late 1950s to the mid-1970s, is now tied for the most Grand Slam singles titles with 24. Court’s best season came in 1970 when she became the second woman to achieve the calendar-year Grand Slam, winning all four major titles. Known for her powerful serve and volley game, Court’s consistency and ability to adapt to different playing conditions made her a formidable opponent. 

T-1. Novak Djokovic – 24 Grand Slams

Serbian superstar Novak Djokovic has etched his name in the annals of tennis history, tying Court’s 24 grand slam titles after winning the 2023 Australian Open, French Open and U.S. Open. Djokovic played a five-set thriller against the young Carlos Alcaraz in the 2023 Wimbledon final but fell just short of what would have been the first men’s singles Grand Slam since 1969. Known for his extraordinary flexibility, mental toughness and defense, Djokovic has dominated all surfaces, making 2023 the second year of his career where he fell one grand slam title short of completing the Grand Slam. His other standout season was 2015, where he won the Australian Open, Wimbledon and U.S. Open—and reached the final of the French Open.

3. Serena Williams – 23 Grand Slams

American tennis legend Serena Williams holds the women’s record for the most Grand Slam singles titles in the Open Era (began in 1968) with 23. Williams’ powerful serve, athleticism and fierce competitive spirit made her a dominant force in women’s tennis. Her best season came in 2015, where she won three Grand Slam titles—Australian Open, French Open and Wimbledon—and came close to completing the calendar-year Grand Slam, falling just short at the U.S. Open. 

T-4. Rafael Nadal – 22 Grand Slams

Representing Spain, Rafael Nadal is widely regarded as the “King of Clay,” dominating the French Open with an unparalleled 14 titles. Nadal’s powerful topspin forehand and tenacity have been key to his success, though retirement is now on his doorstep after battling through injuries for years. His best season arguably came in 2010, when he won three of the four Grand Slam titles—French Open, Wimbledon and the U.S. Open—becoming the youngest player in the Open Era to complete a Career Grand Slam. 

T-4. Steffi Graf – 22 Grand Slams

German tennis icon Steffi Graf is one of the most successful female players in history, with 22 Grand Slam titles. Graf’s best season was 1988, when she achieved the rare feat of winning all four Grand Slam titles in a single calendar year, a Grand Slam, and also secured the Olympic gold medal, completing the “Golden Slam.” Known for her powerful forehand and exceptional footwork, Graf dominated women’s tennis in the late 1980s and 1990s. 

6. Roger Federer – 20 Grand Slams

Swiss maestro Roger Federer is often considered the epitome of grace and elegance on the tennis court. With 20 Grand Slam titles, Federer will forever be first-class. His best season was 2006, during which he won three Grand Slam titles—Australian Open, Wimbledon and U.S. Open—and reached the final of the French Open. Federer’s fluid playing style and slick one-handed backhand earned him fans worldwide. His longevity in the sport and his gentlemanly conduct made him a beloved figure both on and off the court.