It’s safe to say that no sister act has ever been a bigger hit on the New York Stage than Venus and Serena Williams. The two marquee-topping champions have combined for a total of eight US Open singles titles, with Serena capturing six and Venus, two. In the weeks leading up to the 2022 US Open, Hall of Fame tennis writer Steve Flink will be recounting each of those remarkable title runs. In this first installment, Flink takes a look at Serena’s unexpected breakthrough in 1999.
As the curtain closed simultaneously on the 1990’s and the 20th Century in tennis, Americans were celebrating success on the loftiest level , and the sisters Williams—Venus and Serena— were poised to declare their greatness over and over again across the next couple of decades and beyond. In 1997, Venus had reached her first major final at the US Open before losing to the precocious 16-year-old Swiss stylist Martina Hingis. A year later, she made it to the penultimate round of her country’s championships before falling against eventual champion Lindsay Davenport.
With that, many insiders believed that Venus Williams was ready to succeed on the hard courts at the 1999 Open. At 19, she was gaining ground steadily in the women’s game, harnessing her immense power on serve and off the ground, striking fear into the hearts and minds of her rivals with her quiet confidence, crackling ball striking and unmistakable court presence. Venus Williams sorely wanted to win her first major at the US Open.
To be sure, Hingis and Davenport were prime contenders for the crown, but the smart money among many learned observers was on Venus Williams to make the most of her growing stature and come away with the title.
And yet, too many in the game’s cognoscenti were overlooking or underestimating Serena Williams who was still only 17, but clearly moving swiftly toward the top of her game. Serena was improving immensely all across the 1999 season, and her game was now more polished, purposeful and potent than ever before. She could knock the cover off the ball like Venus, but Serena’s service motion was smoother, her court craft in some ways larger, and her will to win perhaps more insatiable.
Serena had accomplished prodigiously over the course of that season, establishing herself as an unswerving match player, making her foremost rivals realize that she was going to give each and every one of them all they could handle. A signature moment for Serena had occurred five months prior to the start of the US Open. Confronting Steffi Graf in the final at Indian Wells, Serena took that prestigious title on the hard courts in California with a clutch performance, overcoming the formidable German a few months before Graf would collect her 22nd and last major championship at Roland Garros. Williams toppled Graf in a stirring generational clash of icons, coming through 6-3, 3-6, 7-5.
Not long before Indian Wells, Williams had secured her first career singles title at the Paris Open indoors. Her landmark triumph over Graf at Indian Wells was her second career tournament victory. She had lost in the third round of the Australian and French Opens that season, and missed Wimbledon with the flu. But, over the summer, Serena secured the title in Los Angeles—her third career WTA crown. Nonetheless, despite all of her accomplishments in 1999, Williams remained a work in progress, a great champion emerging on many levels yet, seemingly, still not fully formed.
But the fact remained that Williams— appearing in only her seventh career major tournament— was unmistakably making serious inroads in the women’s game. She was seeded seventh at the US Open behind Hingis, Davenport, Venus Williams, Monica Seles, Mary Pierce, and Amanda Coetzer. No women’s seed that low had ever been victorious at the Open. The lowest women’s seed to capture this event prior had been Great Britain’s Virginia Wade at No. 6 in the inaugural year of 1968.
Dropping only seven games across four sets and two convincing matches on her way to the third round, Serena took on the sprightly Kim Clijsters. The fleet-footed Belgian opened up a 5-3 final set lead over Serena in a spectacularly fought battle. But Williams recorded a career defining triumph, sweeping four games in a row and 16 of the last 17 points to win 4-6, 6-2, 7-5. She then came from behind mightily again to oust No. 16 seed Conchita Martinez, the 1994 Wimbledon champion, prevailing 4-6, 6-2, 6-2 in that encounter.
Now in the quarterfinals, Williams found herself down a set once more, this time against the two-time Open victor Seles. But Serena raised her game decidedly to overcome the heavy-hitting left-hander 4-6, 6-3, 6-2. With growing assurance, she controlled the tempo of the contest over the last two sets, winning 12 of the last 17 games.
Next on the agenda for Williams was a semifinal appointment with the defending champion Davenport. Their three-set collision was well played on both sides of the net, pitting Davenport’s extraordinarily clean ball striking off both sides and excellent anticipation against Serena’s superior speed, athleticism and power. Davenport was masterful when allowed to take control from the center of the court, sending her shots deep into the corners and stifling Williams in the process. But, ultimately, Serena was much better than Davenport on the run and her shot-making prowess ruled the day as she won that pulsating skirmish, a fourth consecutive three set match against a front-line player.
That put her in good stead heading into a final-round duel against the 1997 champion Hingis. The 18-year-old Swiss had overcome Venus Williams in three hard and tumultuous sets, and a good many longtime observers believed Hingis’ outstanding ball control, subtle variations of pace and strategic acumen would carry her past Serena Williams as well.
The meticulously prepared Hingis had already captured all five of her career major titles, and her experience on the premier stages of the sport made the Swiss the favorite in this contest. But Williams played the big points remarkably well in the opening set, saving break points in all five of her opening-set service games, taking that set, 6-3. When Williams surged to 5-3 in the second set and reached double match point in the ninth game, a straightforward victory seemed well within her grasp.
At that juncture, however, Serena was understandably apprehensive. She lost three games in a row and almost conceded the set. But, at 5-6, Williams saved a set point. In the ensuing tie-break which was locked at 4-4, Williams hit out freely to collect three crucial points in a row for her first Grand Slam tournament triumph: a 6-3, 7-6 win.
In succession, Serena had toppled the three-time future US Open champion Clijsters, 1994 Wimbledon champion and eventual Hall of Famer Martinez, two-time US Open victor Seles, defending champion Davenport and 1997 champion Hingis—the No. 1 seed. She had collected five consecutive victories over top-of-the-line opposition. It was a monumental breakthrough victory for a player destined to establish herself as one of the greatest players of all time.
Defeating so many formidable competitors was abundant proof that Serena Williams' maiden win at a major was in many ways meant to be. She became the first Black woman to win a Grand Slam tournament in singles since Althea Gibson took her second straight U.S. Championships title at Forest Hills in 1958.
Despite her bruising semifinal loss to Hingis, Venus Williams was there courtside to cheer on Serena in the final. Serena was deeply appreciative of her older sibling’s support, especially under the circumstances.
As Serena said afterwards, “Venus was up there supporting me. After I lost my first two match points, I looked over to not my Mom and my Dad—I saw them also—but I saw Venus over there really making sure, pumping me up. It really helped me so much.”
Asked about being the first Black woman since Gibson to rule at her country’s championships, Williams responded, “It’s really amazing for me to even have an opportunity to be compared to Althea Gibson. She was a great player. It’s pretty exciting for me. I actually went out and won a Slam. That’s great.”
There would, of course, be many more for Serena—22 more and counting to be precise. But her 1999 triumph in New York at the US Open was the launching pad for it all, the beginning of something substantial, the moment when her life and career were altered irrevocably.
Serena Williams took the US Open title before many believed she was ready for that level of success. But it was absolutely no accident that she was victorious. She simply arrived among the elite slightly ahead of schedule.
