Williams announced she was stepping down from the sport earlier this month.
Serena Williams came out on top at the U.S. Open Monday night. Williams kicked off the first match of her retirement tour at New York City's Arthur Ashe Stadium Monday, where she went head-to-head with Montenegrin tennis player Danka Kovinić.
Williams walked away with the win, beating Kovinić 6-3, 6-3 in the first match of what is expected to be Williams' final professional tennis tournament.
Ahead of the match, Williams was introduced as the "greatest of all time," walking onto the court in a glittering ensemble, which featured six layers to represent her six U.S. Open wins. There, she was greeted by a stadium filled with adoring fans who cheered her on, including her daughter, Olympia, who matched her mom in her own sparkling, black fit. Olympia's look also served as a call back to her mom's early days on the court, with the four-year-old sporting beaded braids, which Williams often rocked when she was starting out.
Williams later took off a few layers of the look to reveal a black figure skating-inspired Nike dress, which she designed and played in Monday night. The tennis dress featured a diamond-encrusted bodice and a matching headband. Her NikeCourt Flare 2 shoes included a diamond-encrusted Swoosh and solid gold lace deubrés with 400 hand-set diamonds.
Williams' look wasn't the only thing that sparkled. The match also featured quite the star-studded crowd, including Anna Wintour, Bill Clinton, Queen Latifah, Anthony Anderson, Hugh Jackman, Mike Tyson and more, all on hand to see Williams at the first match on her farewell tour.
While not in attendance, Oprah Winfrey had a special message for the champ, which was delivered in a video shown after the match.
"What's there to say, years went by in a blink," Winfrey said as footage of Williams' storied career flashed across the screen. "'98 feels like yesterday. You've given us so much; all we can do is thank you. Thank you for making the bright lights brighter, and the Big Apple bigger. Thank you for showing us how to be graceful, powerful, fearless. Thank you for dressing to the nines and bringing your dancing shoes. Thank you for turning center court into center stage -- for bringing the house down. Thank you for showing us what it means to come back, and for never, ever, backing down. Thank you for changing the face of the game -- for inspiring the next generation. Thank you for thinking outside the lines and encouraging us to evolve. Thank you for showing us how to love the sport and for always loving us back."
"Just know, whatever you do next, we'll be watching," Winfrey added before ending the heartfelt tribute. "With love, all of us."
Instead of a post-game interview, Winfrey's friend and CBS Mornings host, Gayle King, took the mic and took the chance to praise Williams for her accomplishments both on and off the court, as she congratulated the superstar athlete on her first-round win.
"She's changed the hue of the game, she's changed the complexion of the game, for those who play and those of us who watch it," King said. "And it just made me so, so proud."
Winfrey and King weren't the only ones to shower Williams with love after her win. In addition to the fans, who flashed a giant sign in the stadium that read, "Serena," the tennis pro was given a send-off by another fellow tennis great, Billie Jean King, who thanked Williams for sharing her journey with the world.
"You are fearless. I love it. And you hate to lose. It is great," King began. "You've touched our hearts and minds, to be our authentic self, to use our voices, to dream big."
She continued, "Thank you for your leadership, and commitment to diversity, equity and inclusion. Especially for women and women of color. Most of all, thank you for sharing your journey with every single one of us. We love you, God bless you, and guess what? You're just beginning!"
Next up, Williams is set to play No. 2 seed, Anett Kontaveit of Estonia, Wednesday. While the win means Williams advances to the next round, she also has a doubles match on the books. She is set to play her first doubles match of the tournament with her sister, Venus Williams, also on Wednesday -- though Williams would not confirm whether this will be the last time fans see the sisters on the court as a doubles duo.
Earlier this month, Williams announced her intention to retire from the sport, and while she didn't officially use that word, she did share that she is "evolving away from tennis."
"I’m here to tell you that I’m evolving away from tennis, toward other things that are important to me," Williams shared in a first-person account published in Vogue's September 2022 issue. "A few years ago, I quietly started Serena Ventures, a venture capital firm. Soon after that, I started a family. I want to grow that family."
The 40-year-old star welcomed her first child with her husband, Alexis Ohanian, in 2017. The 23-time Grand Slam winner detailed how the youngster prays for a baby sister and often says she wants to be a big sister -- something Williams and Ohanian have been planning for. "In the last year, Alexis and I have been trying to have another child, and we recently got some information from my doctor that put my mind at ease and made me feel that whenever we’re ready, we can add to our family," she said. "I definitely don’t want to be pregnant again as an athlete. I need to be two feet into tennis or two feet out."
And after all she's been through, it's looking like Williams is taking her feet off the court.
"The way I see it, I should have had 30-plus grand slams. I had my chances after coming back from giving birth. I went from a C-section to a second pulmonary embolism to a grand slam final," she candidly recalled. "I played while breastfeeding. I played through postpartum depression. But I didn’t get there. Shoulda, woulda, coulda. I didn’t show up the way I should have or could have. But I showed up 23 times, and that’s fine. Actually, it’s extraordinary. But these days, if I have to choose between building my tennis résumé and building my family, I choose the latter."
Williams' decision didn't come without plenty of thought and counsel from family, and friends, including Meghan Markle and Prince Harry -- both of whom she discussed her retirement with before releasing the Vogue article.
During the premiere episode of Markle's Archetypes With Meghan podcast, Williams echoed a similar sentiment, telling the Duchess of Sussex, "I’ve been putting it off for so long, and as a woman, there’s only so, so long you can put that off. I’ve been fortunate enough to play tennis really well, but I think my best is being a mom."
While Williams said saying goodbye to the sport is "the hardest thing that I could ever imagine," she hopes her legacy will help future female athletes.
"I’d like to think that thanks to opportunities afforded to me, women athletes feel that they can be themselves on the court. They can play with aggression and pump their fists. They can be strong yet beautiful," she wrote. "They can wear what they want and say what they want and kick butt and be proud of it all," she says. "I’ve made a lot of mistakes in my career. Mistakes are learning experiences, and I embrace those moments. I’m far from perfect, but I’ve also taken a lot of criticism, and I’d like to think that I went through some hard times as a professional tennis player so that the next generation could have it easier."
For more on Williams and her legacy in the sport, check out the video below.