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In 1997, 17-year-old Venus Williams reached the US Open final on her tournament debut, justifying the expectations heaped upon her at an even earlier age.

While the glare of the spotlight was bright, though, she wasn’t the only player in the Williams household who was being hailed as a future star of the game.

Serena Williams, 15 months younger than her older sister, also generated more than her fair share of attention. The year Venus advanced to the championship match in New York, Serena began competing on the WTA Tour in earnest and finished the season ranked just inside the Top 100 at 99. A year later, Serena Williams ended her campaign in the Top 20, during a season that also saw her capture two Grand Slam mixed doubles titles, at Wimbledon and the US Open with Max Mirnyi.

Meanwhile, Venus had established herself as a member of the Top 10, but it wouldn’t be long before the younger Williams joined her there. After winning her first singles title indoors in France in 1999, Serena notched her second first-place showing in a row by triumphing in Indian Wells, defeating none other than Steffi Graf in the final, the German who was the most recent player to secure the calendar-year Grand Slam.

20 years ago: Serena Williams sets the stage for the next millennium

20 years ago: Serena Williams sets the stage for the next millennium

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During the clay-court season, Venus’ momentum slowed down somewhat and injury kept her from playing Wimbledon. When the tour turned to the summer hard-court stretch leading up to the US Open, the Californian resumed her winning ways by claiming the title in Los Angeles, where she defeated four-time Grand Slam titlist Arantxa Sanchez-Vicario and world No. 1 Martina Hingis on her way to the championship.

Ranked No. 11 in the world going into that tournament, her result there lifted her back into the Top 10 with the year’s final major on the horizon.

At her US Open debut in 1998, Venus fell in the third round of singles to Irina Spirlea, whom her sister had defeated in the 1997 semifinals in a match that wasn’t without its share of controversy. Returning to the tournament in 1999, Serena was seeded seventh, four spots behind Venus—a heavy favorite for the title in the best year of her still-burgeoning career.

In the first round, Serena faced fellow American Kimberly Po, who had reached the round of 16 a year earlier and was in the top 15 in 1997. Dropping only one game, Serena raced on to the next round, where she posted another straight-sets win. In the third round, the seventh seed would take on another teenager eager to make her own impact on the game.

20 years ago: Serena Williams sets the stage for the next millennium

20 years ago: Serena Williams sets the stage for the next millennium

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Kim Clijsters, only 16 and already ranked 98th in the world, had beaten two qualifiers in the opening rounds of her US Open debut. Against Serena, she won the first set before dropping the second. In the decider, Serena eked out a 7-5 win to move on against former Wimbledon champion Conchita Martinez. Similar to the Clijsters match, the 17-year-old was again forced to rally from a set down before advancing to her first Grand Slam quarterfinal.

Drawn to face two-time champion Monica Seles, one of her influences, in the final eight, Serena went the distance for the third match in a row to join her sister in the semifinals, who had a much easier time navigating through the draw at this point.

An all-sister final appeared imminent, but while Serena was able to defeat the second seed Lindsay Davenport, Venus fell to top seed Hingis, who had topped her back in that 1997 championship match.

Playing in her first Grand Slam final compared with Hingis’ ninth, it was Serena who got off to the perfect start by taking the first set 6-3 against her 19-year-old foe. In the second, the two stayed on even ground, eventually working their way to a tiebreak. Serving up 6-4, Serena drew one final backhand error from Hingis to clinch the title, her fourth of the year and the first Grand Slam singles championship for the Williams’ household.

20 years ago: Serena Williams sets the stage for the next millennium

20 years ago: Serena Williams sets the stage for the next millennium

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