The Biggest Moments In Serena Williams' Career

If you Google "GOAT athletes," Serena Williams' name is on top. She's included in a list of incredible people, including Babe Ruth, Wayne Gretzky, Tiger Woods, and Muhammad Ali. According to Biography, Serena was born in 1981 in Saginaw, Michigan, but grew up in Compton, California. Under the guidance of her father, she and her sister Venus learned how to play tennis, a sport they would later dominate. 

The siblings would go on to win 14 Grand Slam doubles titles and a slew of singles titles over the course of their careers. But Serena eventually edged out her older sister and won a whopping 23 Grand Slam singles titles — more than any other person. Whether you've followed Serena's career closely or just know the basics, she is undeniably one of the most influential female athletes of the past century. Here are some of the highlights of her life and legacy.

Serena loses her first professional match

Serena was just 14 years old when she traveled to Quebec City in Canada to make her professional debut in The Challenge Bell, according to One year earlier, her sister Venus had kicked off her own tennis career in Oakland, California. At the time, the siblings were training with coach Rick Macci. Prior to participating in the tour, their father Richard Williams prevented them from competing in junior tournaments because he didn't want to expose them to the stress brought on by competition. When it came to Serena, Richard didn't want his daughter to burn out at a young age because she was such a perfectionist.

On the way to Canada, the pair missed a flight and arrived late on the night before the match, so Serena did not have time to practice before the competition. In the first match, she challenged 18-year-old Annie Miller, who was ranked 149 in the world. In what may come as a surprise to Serena's audiences today, she lost 6-1, 6-1. Afterward, Serena said, "I didn't play like I meant to play," and that she thought she played "kind of, like an amateur." Years later, she explained that she had a difficult time dealing with her nerves. She went back home, practiced more, and rejoined the professional circuit. Funnily enough, Miller wound up quitting the sport in 1998. Much of her legacy revolves around being the first person to play against Serena in a professional setting.

She loses to Venus during their first Grand Slam meeting

In 1998, a 16-year-old Serena played her 17-year-old sister Venus for the first time in a Grand Slam tournament. At the time, Venus was ranked 16. Their father had predicted that Serena was going to be a bigger star than her older sister, and some believed that she would defeat Venus in the competition. However, Venus was the one who wound up having the upper hand and advanced to the third round in the Australian Open after beating her sister.

Venus told The New York Times, "Serena hates to lose, and her reputation is she never loses to any one twice." She said she would have preferred to face her sister in the final round, and that it "wasn't so fun" that Serena lost in the second round. For her part, Serena explained that she tried to imagine Venus as just another competitor instead of her sister, but acquiesced that Venus had more experience than she did. Serena was visibly sad when they shook hands following their match. The last time the pair had challenged each other, 8-year-old Serena lost to Venus 6-2, 6-2 in the finals of her first junior tournament.

Serena wins her first Grand Slam doubles title

Early in her career, Serena watched her sister excel while she worked on her own game. Serena finally learned the thrill of victory at Wimbledon in 1998 when she won the mixed doubled title alongside Max Mirnyi of Belarus with a 6-4, 6-4 triumph over Mirjana Lucic of Croatia and Mahesh Bhupathi of India. Venus and her partner, Justin Gimelstob, lost in the semifinals, according to The Washington Post. Neither sister had yet won any Grand Slam singles titles, but together they had amassed three Grand Slam titles in mixed doubles. Venus won hers at the Australian and French Opens, both with partner Gimelstob in 1998.

Venus was visibly thrilled when her younger sister won the mixed doubles competition and danced in the stands after Serena busted out some moves on the court. Serena and her partner had played two matches that day, and the teenager was also nursing a calf injury she sustained from a singles match, forcing her to drop out of the singles competition in the middle of the third round and preventing her from playing doubles with her sister.

Serena wins her first Grand Slam singles title

On September 11, 1999, Serena took home her first Grand Slam singles title at the U.S. Open in Flushing Meadows, New York. She was just 17 years old and achieved the singles victory before her older sister, Venus, according to Serena's opponent in the final round was Martina Hingis, from Switzerland, who was considered a teenage prodigy in the sport as the youngest person to claim a world No. 1 ranking at just over 16 years old. Prior to getting matched with Hingis, Serena claimed her first title in Paris Coubertin, where she beat Amélie Mauresmo. Gaining momentum, she also beat Steffi Graf at Indian Wells in the same year.

Although she pulled out of Wimbledon to rest an injury, Serena won yet another tournament in California the summer before she head to the U.S. Open. On facing Venus in the semi-finals before challenging Serena in the finals, Hingis commented, "They're three against me. With talking, I can't beat them. I know that. So I have to try to beat them on the court." Hingis did overcome Venus but wasn't as fortunate with Serena, who beat Hingis in the tie-breaker. Her next Grand Slam title would come three years later.

Serena wins several Olympic gold medals

At the 2000 Olympic Games in Sydney, Australia, Venus won a gold medal in the singles competition. Serena, ranked No. 8 in the world, didn't enter the singles competition because each country could only have three representatives and the other two American competitors were Lindsay Davenport and Monica Seles (all ranked in the top five in the world), per However, Venus' gold wasn't the only medal the Williams family would bring home that Olympics.

The siblings' triumph at the Olympics was significant for several reasons. First, they were the first sisters to win an Olympic gold medal in the doubles competition. Second, Venus was the first person since Helen Wills in 1924 to take home gold for both singles and doubles. Finally, they were also the third consecutive U.S. pair to win the gold medal in doubles. 

In their final match, the sisters took down Miriam Oremans and Kristie Boogert 6-1, 6-1 in less than 50 minutes. The moment was special for Serena because she only had the opportunity to take home an Olympic gold medal every four years, whereas Grand Slams happened annually. But Olympic golds would also become a regular achievement for the Williams sisters. The pair won gold medals in doubles at the 2008 Olympics in Beijing, China. They repeated the feat in 2012 at the Olympics in London, England, where Serena also took home a singles title.

Serena beats Venus to win the French Open

Despite the obvious competitive nature of the sport, Serena and Venus remained close while they faced each other on the court and even lived together in South Florida. They faced off at the French Open in June 2002 and took home first and second place at the event, according to Sports Illustrated. Throughout the tournament, the sisters prevailed against tough opponents such as Monica Seles and Jennifer Capriati. Former player and TV commentator Nathalie Tauziat said of the duo: "Right now they're clearly dominating. The scary thing is, they're just starting to enter their prime years."

In the final round of the competition, Serena beat her sister 7-5, 6-3, and took home the title. It was the second major of her career and placed the sisters in the No. 1 and No. 2 rankings. The rounds between the two weren't' particularly exciting. Although Sports Illustrated described these types of family matches as "stinkers" — likely due to the similarities in play developed by having the same coach and growing up together — Roland Garros notes these "jangly nerves" were mixed with "jaw-dropping tennis" on the part of both players.

Serena reaches World No. 1 ranking

One month after facing each other at the French Open finals, the Williams sisters competed at Wimbledon. Venus came into the event as the two-time defending champion, but she lost to Serena 7-6 (4), 6-3. The win pushed Serena into the No. 1 spot in the world rankings after not dropping any sets at Wimbledon and winning 19 matches in a row throughout the season, according to ESPN.

This was Serena's second consecutive Grand Slam win, and the match that brought her the title was more riveting than the duo's more "lackluster" prior performances, per ESPN. One advantage Serena held over Venus was that the older sister was nursing a shoulder injury. When asked about it, Serena said, "Unfortunately, it's like a war out there. If there's a weakness, someone's going to have to be attacked." Still, their professional rivalry didn't extend to their personal relationship: ESPN reported that Serena removed a stray lash from Venus' eye during their conversation after the match. For her part, Venus didn't seem to have any hard feelings. After losing, she continued to look out for her sister by instructing Serena to curtsy, a tradition Venus was unaware of her first time winning Wimbledon.

Serena earns her first career Grand Slam

Does it get any better than earning the No. 1 world ranking? You bet it does. Following Wimbledon in the summer of 2002, Serena defeated her sister at the 2002 U.S. Open. This set her up to hold all four Grand Slam titles at the same time — a feat last achieved by Steffi Graf in 1994, according to When the Williams sisters once again faced off in another Grand Slam final at the Australian Open, Serena won 7-6, 3-6, 6-4. It was the fourth time in a row that the pair were matched in a Grand Slam final. As a result, Serena's 2003 triumph became dubbed the "Serena Slam" and the "Sister Slam."

Richard Williams had predicted years earlier that his daughters would be ranked first and second in the world, and his dream became a reality. Serena admitted the achievement made her more emotional than normal and "really, really, really happy." No doubt!

Serena makes a career comeback in 2007

It can be difficult to maintain one's spot at the top, and it was no different for a powerhouse such as Serena Williams. After developing a knee injury in 2006 and taking a six-month hiatus following the Australian Open, Serena competed in just three events and didn't even make the top 100, according to Tennis Australia. In 2007, she lost in the Hobart International quarterfinals to Sybille Bammer. Losing in a low-tier event like this was crushing for Serena. She had gained about 20 pounds and had to deal with commentary about her weight and subsequent disappointing performances. But she still had a fire in her and wouldn't let other people's opinions shape her game. 

She kicked it up a notch at the 2007 Australian Open. It was the athlete's first major final in two years, and her opponent was Maria Sharapova. According to Tennis Australia, their match is considered "one of the great Grand Slam final performances in the sport's history." Serena won 6-1, 6-2 to take home her eighth Grand Slam singles trophy. The victory was particularly sweet because of all the negative things people were saying about her. She explained: "I get the greatest satisfaction just holding up the Grand Slam trophy and proving everyone wrong."

She wins four Grand Slams in a row ... again

When Serena won her first Grand Slam in 1999, she became the first African American woman to win a singles major since the Open Era began in 1968, according to Sky Sports. She continued to accumulate Grand Slams over the course of her career. In 2010, she won her 12th Grand Slam singles title at the Australian Open, matching the record held by Billie Jean King. At Wimbledon in the same year, she earned her 13th Grand Slam title at 28 years old. Before retiring, she would nearly double King's record.

The record-breaking wins were put on pause in 2012 when Serena took some time off before competing at Wimbledon and the U.S. Open due to a leg injury and pulmonary embolism. But once she returned in 2013, she again won the French Open and U.S. Open. And 2015 turned out to be an even more incredible year for the tennis star. She won the Grand Slam titles at the U.S. Open, Australian Open, French Open, and Wimbledon, remarkably completing the "Serena Slam" for a second time.

She wins her 23rd Grand Slam singles Title while pregnant

In 2017, Serena won her record-breaking 23rd Grand Slam singles title at the Australian Open But what makes the feat even more remarkable is that she did so while eight weeks pregnant, the BBC notes. The early stages of pregnancy are very difficult for many women. With the body going through immense changes, fatigue, morning sickness, and nausea are all common symptoms that can make even simple tasks like getting out of bed or eating breakfast difficult — much less the rigorous athletic activity required to win a professional tennis match. However, exercise is a good thing to keep up in pregnancy and can help with some of these side effects, per the BBC. 

Once again beating her sister in the final, Serena didn't drop a single set at the Australian Open that year. And she did it all while growing a new life in her belly. As many fans took to social media to claim: She really is the GOAT. 

She plays her last U.S. Open match

Unfortunately, good things must come to an end, and Serena announced in a 2022 issue of Vogue that she was stepping down from the sport she loved so much. (Though she avoids the word "retirement" and prefers to think of her transition as an "evolution.") Serena wrote that she recognized at the age of 41 that she couldn't continue playing while growing her family. Ultimately, she decided to pursue other avenues, including her venture capital firm. The choice to stop playing professionally was very painful for Serena because her entire life revolved around tennis. Although she noted that she does sometimes think about how she didn't quite surpass Margaret Court's 24 Grand Slam titles before the "Open Era" began in 1968, she says "these days, if I have to choose between building my tennis résumé and building my family, I choose the latter."

Her last attempt at a title was the 2022 U.S. Open. However, Serena lost in the third round against Ajla Tomljanovic 7-5, 6-7 (4), 6-1, reported NPR. After winning, Tomljanovic said, "I just thought she would beat me ... She's Serena. That's just who she is: She's the greatest of all time. Period."