Ranking the Top 25 Tennis Players of the 21st Century (So Far)

Ranking the top 25 players who have had the greatest achievements of the past 25 years.

Roger Federer at the 2014 Cincinnati Masters. | IMAGO / ZUMA Press Wire

Four players with 20-plus major singles titles to their names. Years spent at the top of the standings. Career Grand Slams many times over. The 21st century has seen astronomical feats pulled off by past, present and future legends of the game.

Sports Illustrated's Serve On SI has counted down the top 25 players who have already left an indelible mark as the sport enters the second quarter of the millennium.

25. Andy Roddick

Andy Roddick at the 2008 Sony Ericsson Open. | IMAGO / ABACAPRESS

The last American man to win a Grand Slam singles title, Andy Roddick, was one of the most consistent players on the men’s tour during the Aughts. The 2003 US Open champion stayed in the top 10 of the singles rankings for nine consecutive years and reached four more Grand Slam finals, falling to Roger Federer each time.

24. Daniil Medvedev

Daniil Medvedev at the 2019 Miami Open. | IMAGO / Depositphotos

The only member of the post-“Big 4”/pre-Sinner-Alcaraz generation to make it to number one, the Russian’s on-court accomplishments include a U.S. Open win, five other major title-tilt appearances and an ATP Tour finals triumph. Daniil Medvedev isn’t one for settling into a particular comfort zone: His 21 tournament victories have come at 21 different tournaments.

23. Simona Halep

Simona Halep at Wimbledon 2019. | IMAGO / Hasenkopf

A member of the top 10 for seven years straight, Simona Halep was a consistent challenger for the sport’s biggest prizes over the course of her career. The former world No. 1, who reached the pinnacle of the rankings before winning a Grand Slam title, did pick up two of them in consecutive years: the 2018 French Open and 2019 Wimbledon.

22. Angelique Kerber

Angelique Kerber at the 2018 Australian Open. | IMAGO / Newscom World

After establishing herself as a consistent member of the top 10, Angelique Kerber’s ascent really took off in 2016. The German won the Australian and U.S. Opens for her first two Grand Slam titles, and made the finals of the Olympics that year.

Two years later, the former world No. 1 captured the most prestigious prize of them all, Wimbledon, beating Serena Williams in the final, her second win over the American in a major championship match after Melbourne.

21. Jennifer Capriati

Jennifer Capriati at Wimbledon 2001. | IMAGO / Eisele

Starting her professional career in 1990 with a nearly unprecedented amount of hype behind her, Jennifer Capriati experienced a series of ups and downs on and off the court throughout the decade. Toward the end of the ‘90s, she was in full-on comeback mode, and in 2001, expectations were met when she won the 2001 Australian Open, the first of three Grand Slam singles titles. Capriati would also earn a spot at the top of the rankings, on her way to that anticipated spot in the Hall of Fame.

20. Stan Wawrinka

Stan Wawrinka at the 2017 French Open. | IMAGO / AFLOSPORT

Stan Wawrinka breaking through the dominance of the ATP’s “Big 4” to win a Slam, like Marin Cilic and Juan Martin del Potro did, was truly impressive. Triumphing on three occasions, however, is legendary.

Armed with arguably the best one-handed backhand of all time, the Swiss won titles at the Australian, French, and U.S. Open in a three-year stretch to essentially earn a spot in the Hall of Fame after his career is over—whenever that might be. “Stan the Man” is ready to take on the 2026 season at 40 years young.

19. Kim Clijsters

Kim Clijsters at the 2011 Australian Open. | IMAGO / Belga

At only 20 years old, Kim Clijsters made it to number one in the world in both singles and doubles, but the ultimate achievement of solo success at a major eluded her. That changed two years later when she won the U.S. Open for the first time. In 2009, the Belgian claimed the title in New York again in remarkable fashion. 

Having stepped away from the game to become a mother, Clijsters returned to the tournament that year, unranked, and finished it as the champion. She’d add another U.S. Open to her title haul and an Australian Open before stepping away from the game again.

18. Mike Bryan and 17. Bob Bryan

Mike and Bob Bryan in the 2016 Davis Cup World Group stage. | IMAGO / ZUMA Press Wire

First-ballot Hall of Fame inductees this year, Mike and Bob Bryan dominated the men’s doubles game for the bulk of the 21st century, with their achievements likely to go unmatched. Together, the brothers won 119 titles, with 16 of those coming at the Grand Slam level. They’re the only doubles specialists to win all four majors, the year-end finals, all of the Masters 1000 tournaments, Olympic Gold, and a Davis Cup title.

16. Andre Agassi

Andre Agassi at Wimbledon 2003. | IMAGO / Claus Bergmann

Andre Agassi closed out the 20th century on top of the tennis world, having completed the career Grand Slam at the 1999 French Open and capturing his fifth major at the U.S. Open later in the year. Through the first five years of the new millennium, the Las Vegas native—whose career started as a teen in the 1980s—stayed among the world’s top 10, adding three more Grand Slam titles to his career haul.

15. Lleyton Hewitt

Lleyton Hewitt at the 2005 Australian Open. | IMAGO / Ray Giubilo

In 1998, the 16-year-old Australian announced himself to the tennis world by becoming one of the youngest players ever to win a singles title. By the time of the 2001 U.S. Open, Lleyton Hewitt was poised for a major breakthrough, fully accomplished by topping Pete Sampras in the final, which propelled him to the year-end top spot. The next year saw him win another major—this time Wimbledon—and finish on top again.

14. Ashleigh Barty

Ashleigh Barty at the 2022 Australian Open. | IMAGO / Newscom World

It’s truly one of the sport’s greatest comeback stories: Citing a desire to do more outside of tennis, Ashleigh Barty retired at the age of 18 as an established doubles standout.

After a two-year break—which included time spent playing pro cricket—the Australian made her return to the tour better than ever. Her crafty game took her to the top of the singles rankings, winning three Grand Slam titles along the way. In 2022, she decided to retire again, holding the number-one spot at the time.

13. Naomi Osaka

Naomi Osaka at the 2021 Australian Open. | IMAGO / Hasenkopf

Of Naomi Osaka’s seven career singles titles to date, four have come at the Grand Slam level, when she claimed a hard-court major a season from 2018 to 2021. Behind her powerful baseline game and serve, the Japanese star also reached No. 1 in the world, gaining global icon status in the process. 

After becoming a mom for the first time, Osaka’s comeback really picked up traction last summer, when she got back into the world’s top 15 and came within points of playing for a fifth Slam.

12. Maria Sharapova

Maria Sharapova at the 2014 French Open. | IMAGO / ABACAPRESS

Win your first Grand Slam title at 17 against the two-time defending champion and the odds are that you’re going to have a noteworthy career of your own. That was truly the case with Maria Sharapova, who shocked Serena Williams in the 2004 Wimbledon final. The Russian, whose Q-rating and on-court accomplishments ran neck and neck, won the career Grand Slam, including two titles on her worst surface, clay, at the French Open.

11. Justine Henin

Justine Henin at the 2006 French Open. | IMAGO / Paul Zimmer

Given her less-than-imposing physical stature, Justine Henin could have gone the route of a baseline scrambler on the court. Instead, she went the opposite direction, playing aggressively and going toe-to-toe with the Williams sisters, Lindsay Davenport, and other heavy hitters of her time. The Belgian did more than her fair share of winning those matches, too, especially on the biggest stages: From 2003 to 2007, she won seven Grand Slam singles titles.

10. Aryna Sabalenka

Aryna Sabalenka at the 2025 US Open. | IMAGO / ABACAPRESS

Possessing one of the most physically imposing games in women’s tennis history, Aryna Sabalenka has been the victor at multiple Slams and reached the top spot in the rankings. And it appears she just keeps getting better. 

The current world No. 1 is coming off a season where she reached the finals of three of the four majors, winning one at the U.S. Open. Over the course of the past two years, the Belarussian advanced to 16 title fights, among the most on the WTA Tour.

9. Andy Murray

Andy Murray at the 2016 Summer Olympics. | IMAGO / Sven Simon

Though his overall Slam triumphs pale in comparison to Djokovic, Federer, and Nadal’s, the Scot stood firmly among them and earned his place in the “Big 4.” Andy Murray won three majors over his career, most famously Wimbledon in 2013, when he became the first British male to capture the tournament in decades. Injuries plagued him in his final years on tour, but not before he finished 2016 at the top of the rankings.

8. Jannik Sinner

Jannik Sinner at the 2025 Australian Open. | IMAGO / Hasenkopf

Already Italy’s winningest Grand Slam singles player after a two-season stretch, it appears Jannik Sinner could be in line to match the feats of the winningest major champions—or even surpass them.

He is arguably the best hard-court player competing right now, but as he demonstrated in 2025, he’s comfortable on any surface. After dropping a heartbreaker in the Roland Garros final this year, Sinner bounced back to claim his first Wimbledon title, putting three of the four majors firmly under his belt.

7. Carlos Alcaraz

Carlos Alcaraz at the 2025 French Open. | IMAGO / ABACAPRESS

Imagine the best attributes of Roger Federer, Rafael Nadal, and Novak Djokovic rolled into one player, and you have the 22-year-old from Spain. Carlos Alcaraz has already won six majors, with only the Australian Open missing from his collection, and has racked up a number of records and accolades in his still-young career, including finishing 2025 at the top of the rankings.

6. Iga Swiatek

Iga Swiatek at the 2024 French Open. | IMAGO / justpictures.ch

When Ashleigh Barty unexpectedly announced her retirement in 2022 while at the top of the rankings, Iga Swiatek took the baton and ran with it, rattling off a 37-match winning streak—the longest on the WTA Tour this century.  Swiatek has won four French Open titles; a U.S. Open crown; and perhaps, most unexpectedly, a Wimbledon title, which she clinched this year in dominant fashion.

5. Venus Williams

Venus Williams at the 2017 Championships at Wimbledon. | IMAGO / Xinhua

Baby sister Serena beat Williams to the punch as a Grand Slam singles champion in the prior millennium. Perhaps that was the inspiration she needed because less than a year later, in 2000, Venus would be crowned the champion at Wimbledon, the first of her five titles there.

She would win seven singles Grand Slam titles in all and spent significant time in the rankings penthouse. Williams reached two major finals in 2017, 20 years after making a title tilt for the first time, a testament to her longevity.

4. Rafael Nadal

Rafael Nadal at the 2020 French Open. | IMAGO / Panoramic by PsnewZ

Two-time Australian Open champion. Two-time Wimbledon champion. Four-time U.S. Open champion. Fourteen-time French Open champion.

When the 19-year-old Spaniard won Roland Garros for the first time back in 2005, the sport had not seen anything like it. Rafael Nadal pummeled the ball and played to win every point like it was his last. That level was evident every time he took the court as he redefined clay-court tennis, while making his presence felt on his opponents—no matter the surface.

3. Roger Federer

Roger Federer at the 2018 Australian Open. | IMAGO / ZUMA Press Wire

It is hard to imagine a bigger “passing-the-torch” moment in tennis than the 2001 Wimbledon fourth-round encounter between the seven-time champion and the 19-year-old Roger Federer, won by the Swiss in five sets.

Though he didn’t win that year, Federer would go on to claim the title two years later, kicking off a near-unprecedented run of dominance. One of the sport’s greatest icons, Federer won 103 singles titles in his career, with 20 of those coming at the Grand Slam level, where he was the first to blow past a seemingly unbreakable record, Sampras’ 14 major wins.

2. Novak Djokovic

Novak Djokovic at the 2024 Championships at Wimbledon. | IMAGO / Propaganda Photo

Even after he won his first Grand Slam singles title at the 2008 Australian Open, it wasn’t entirely clear how much of an impact he would have on the game or whether he would be able to break through the Federer-Nadal stranglehold. As it turns out, any doubts have long been done away with.

The Serbian superstar has outlasted his peers in the “Big 4,” while rewriting the record books nearly every time out. Novak Djokovic is the leader in men’s Grand Slam singles titles; he has won all the Masters 1000 events multiple times over, and thrived in international competition, with Davis Cup and Olympics glory.

1. Serena Williams

Serena Williams at the 2014 US Open. | IMAGO / Depositphotos

Like Agassi, Serena Williams closed out the prior millennium with a Grand Slam title at the 1999 US Open. Capturing a first major before she was out of her teens indicated that she would be one to watch in the new millennium. She took that notion steps further and actually became the one to watch.

From the time she entered her first tournament in the late 1990s until her retirement in 2022, Williams was arguably the biggest name in tennis, with her impact felt both on and off the court.

Dominating opponents with a powerful all-around game and an indomitable will to win, Williams won a career Grand Slam multiple times over in both singles and doubles, as well as multiple Gold Medals at the Olympics, and is only the third woman to be ranked number 1 for more than 300 weeks.

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