On September 26, 2025, tennis legend Serena Williams celebrated her 44th birthday. For tennis fans around the world, it’s more than just a date on the calendar—it’s a reminder of the legacy left by one of the greatest athletes to ever step on court. Throughout her illustrious career, she captured 73 titles, including 23 Grand Slam Championships. Alongside her sister Venus Williams, she secured 14 doubles titles and earned four Olympic medals (one in Singles and three in doubles).

Williams’ career was not just about titles but about moments. Moments that shook stadiums, broke records, inspired millions, and defined what it meant to be the G.O.A.T. 

Let’s take a walk down memory lane through five matches that made Serena Williams the queen of modern tennis:

1. 1999 US Open Final: Serena Williams vs Martina Hingis

Serena Williams started playing tennis at the age of four. Her father homeschooled her and her elder sister, Venus Williams. Right from a very young age, both of them were “brainwashed” to become the number one.

Serena Williams made her professional debut in 1995 at the age of just 14. It took her four long years to taste success on the Grand Slam level. 

The story begins in New York, where a 17-year-old Serena Williams defeated the likes of the defending champion, Lindsay Davenport, and the world number one, Martina Hingis, in the SF and final, respectively, to secure the title at the 1999 US Open. In the final, her fearless hitting and unshakable belief carried her to a 6-3,7-6(4) victory. It was her first of an eventual Open Era record of 23 major women’s singles titles. With that win, she became the first African American woman in the Open era to win a singles major and the first since Althea Gibson at the 1958 U.S. National Championships.

After winning the first set quite easily, Williams got the chance to serve out the match, but she was forced into a tiebreaker by Hingis. However, despite all the pressure, the youngster managed to keep her calm and wrapped up the match in her favor. 

While sharing her thoughts about that match later on, Serena Williams said, “I was really mentally tough out there. I wouldn’t give in to anything. There comes a time when you have to stop caving.” Even her sister, Venus Williams, was also in the stands that day watching her take revenge for her own SF loss to Hingis. “I saw Venus over there really making sure, pumping me up. It really helped me,” said Serena.

So, that’s how the floodgates had opened and the Serena era begun!

2. 2002 Wimbledon Final: Serena Williams vs Venus Williams

This match wasn’t just about Serena; it was about the Williams sisters redefining the sport. The emotional embrace between the sisters at the net symbolized a new dynasty in tennis, and the world knew they were witnessing history.

When she started out on Tour, Serena felt she would always be known as ‘Venus’s little sister.’ However, when Serena won the first of her seven Wimbledon titles, she gifted fans the chance to witness the transition of power from one sister to the other.

She won the first set after a closely fought tiebreaker before wrapping up the second one much more comfortably. The match ended at 7-6(4),6-3 in favor of Serena Williams. She didn’t lose a set in that tournament, and she also became the world number one for the first time after winning the championships. With that win, she also achieved the ‘Channel Slam’ (winning the French Open and Wimbledon in the same year), the first time the feat was achieved since Steffi Graf’s heroics in 1996.

Interestingly, in her post-match press conference, she was asked if this is the fulfillment of a sort of lifetime ambition, winning here at SW19? In reply, Williams said, “I can’t become satisfied because, you know, if I get satisfied, I’ll be like, ‘Oh, I’ve won Wimbledon, I’ve won the US Open. Now, can I relax?’ And it was an extra bonus for me to win the French. Sure, I really wanted to win the French. I mean, I just couldn’t even believe I won. But I just wanted Wimbledon. I wanted to become a member of so much prestige, so much history. I want to be a part of history.”

3. 2003 Australian Open Final: Serena Williams vs Venus Williams

The sun beat down hard on Melbourne, but inside the arena, it was something else entirely that day—quite electrifying. Two sisters stood across from each other once again.

Serena Williams was chasing something historic. A win over her sister Venus would give her four consecutive Grand Slam titles—the so-called ‘Serena Slam’—and confirm, once and for all, her arrival not just as a star, but as a dominant force in the sport.

In that hard-fought battle, Serena defeated Venus by 7-6(4),3-6,6-4. It was Venus Williams' record fourth consecutive runner-up finish at a major, losing every final to her younger sister. For Serena, it was just about adding yet another feather to her cap.

Only six women had ever held all four major titles at the same time, with the 21-year-old Serena adding her name to that illustrious list after that emotional win over her elder sister. While sharing her thoughts after the match, she said, “I never get choked up, but I'm really emotional right now.”

4. 2012 Wimbledon Final: Serena Williams vs Agnieszka Radwanska

On July 7, 2012, as Serena Williams fell to her knees on Centre Court after defeating Agnieszka Radwanska in the Wimbledon final, the tennis world witnessed something deeper—the rebirth of a queen who never truly surrendered her crown. By 2012, Serena had already faced personal and health struggles that threatened her career. At Wimbledon, she reminded everyone who she was.

Smashing 102 aces across the tournament, Serena powered her way to her fifth Wimbledon title. Against Rawanska in the final, she delivered with trademark precision, lifting the trophy as if nothing—not injury, not doubt—could hold her back. She defeated the Pole by 6-1,5-7,6-2.

Why was this match so special? Well, her former coach Patrick Mouratoglou once shared an interesting story about this. He said, “We started together in 2012. She didn’t win a Grand Slam for 2 years when we started, and she lost in the first round of the Roland Garros, and then she called me, and then we started the next tournament in Wimbledon. And she won Wimbledon in singles and doubles, and then she won the Olympics three weeks later. Gold medal in singles and doubles! Then we go to the US Open, she wins the US Open, and at the end of the season, she wins the Masters, and she comes back to number one.”

Before this title triumph, her last success at the Grand Slam events came way back in 2010 at the Wimbledon Championships. So, this victory had indeed helped her regain faith in her own abilities and rebuild confidence for the rest of her path towards becoming a tennis great.

But interestingly, Mouratoglou claimed that, after finishing the year with seven WTA singles titles and two Grand Slam triumphs, Williams expressed her sadness over missing out on the chance of winning the French Open title for ten long years and asked him to make a plan for her. This showed her never-ending hunger for success. And, in 2013, she defeated Maria Sharapova to win the French Open title.

5. 2020 ASB Classic Final: Serena Williams vs Jessica Pegula

She had 23 Grand Slam titles, four Olympic gold medals, and a record of spending 319 weeks as the world number one in women’s singles. But on January 12, 2020, under the warm New Zealand sun, Serena Williams held a different kind of trophy—one that carried the weight of motherhood, struggle, and quiet perseverance. It had been nearly three years since her last singles title. And this one was for someone special: her daughter Olympia.

She defeated her compatriot Jessica Pegula in the final by 6-3,6-4. It was Williams’ 73rd and last WTA Tour-level singles title and her first since giving birth to Olympia.

During an interview with CNN, she revealed that she “almost died giving birth.” But she remarkably made a return to the Tour six months later in March 2018. After her return, although she reached the finals at Wimbledon and the US Open in both 2018 and 2019, she had to wait a bit to taste her first title triumph after becoming a mother.

So, after finally fulfilling her wish in Auckland, she said, “Oh, it feels good! It’s been a long time. I think you could see the relief on my face. It’s pretty satisfying just to get a win in the final.”

Surely, there are plenty of such matches, which stand tall in Serena Williams’ illustrious career, but these were our picks. Which match do you think should also have been in this list?

Written by

Sayantan Roy

Sayantan Roy is a seasoned tennis journalist at EssentiallySports. He brings a deep tactical understanding to his coverage, breaking down head-to-head records, match dynamics, and on-court strategies with precision. For more than two years, Sayantan has been a key member of the Live Events desk, delivering real-time insights and data-backed predictions for the platform’s Matchday Preview section. His analytical approach has sparked editorial debates and drawn recognition from respected tennis voices, including commentator and analyst Olly_Tennis. Combining his experience in writing with a passion for insightful sports journalism, Sayantan’s work serves as a trusted reference point for tennis fans around the world.

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