With the US Open less than a week away, Serena Williams is the player to beat in the Big Apple. With a 48-2 record in 2015, the world number one is playing the best tennis of her career. Last month, she completed the Serena Slam which means she has won every single Grand Slam since the 2014 U.S. Open all the way until the 2015 Wimbledon Championships. Now, she is looking to be the first player since Steffi Graf in 1988, to win the Calendar Grand Slam. The current world number one is also looking to tie Graf for her 22nd Grand Slam singles title. But who could forget her maiden Grand Slam title where she won the U.S. Open in 1999?

Before the 1999 U.S. Open

Serena Williams was one of the rising stars of the WTA. After her professional debut at the age of 14 in September 1995, the young American had climbed into the world’s top 10 thanks to her breakthrough season in 1999, leading up to the U.S. Open. After two extremely tight losses to Steffi Graf and Sandrine Testud in Australia, Williams was looking to find some momentum on the professional level. Serena’s father Richard Williams had decided that he wanted his girls (Serena and Venus) to spend more time on the practice courts rather than playing junior tournaments so he could prepare them for the professional tour. As a result, Serena had trouble in her first few years on the WTA. But all of that changed in 1999 after the Australian swing as the then 17-year-old Serena made four finals before the U.S. Open that year, winning three of them - the Paris Indoors event, Indian Wells and Los Angeles.

The American looked to be in great form on the hard courts and as a result, she came into the 1999 U.S. Open seeded seventh. With the likes of Martina Hingis, sister Venus Williams and fellow Americans Lindsay Davenport and Monica Seles, no one was really expecting the 17-year-old to win the title that year. Many didn’t think she or her sister Venus were the real deal yet as they were still teenagers at the time and both never won a Grand Slam title before the U.S. Open in 1999 either.

Routine Wins for Serena in her Opening Two Rounds

In the opening round, Williams faced world number 80 and compatriot Kimberly Po. Serena looked to be in fantastic form, demolishing Po 6-1, 6-0. In the second round, the American faced Croatian qualifier Jelena Kostanić. Kostanić gave Williams some trouble but in the end, Serena was too strong for the world number 128. She won 6-4, 6-2 to advance to the third round, equaling her best result at the U.S. Open.

Epic Match with Kim Clijsters in the Third Round

After advancing in straight sets to the third round, Serena was up against a much greater challenge in fellow teenager Kim Clijsters. Clijsters was ranked 98 in the world and she was only 16-years-old at the time, but she sure didn’t play that way. With great athleticism and consistency from the Belgian, Clijsters won the opening set 6-4.

Williams was not going to let this match slip out of her grasp though as she began to play better and better as the second set went on, eventually clinching it 6-2. Now at one-set all, the match was getting interesting. With both players pushing each other to the limit, no one knew which way this match would go. Serena’s powerful hitting matched against Kim’s athleticism and great anticipation seemed to fit together perfectly for a great match. Clijsters served for a place in the second week of the U.S. Open at 5-3 but in a stunning comeback from Williams, she managed to win 16 of the 17 points to win four games in a row, ultimately defeating the young Belgian in a mid-day thriller, 4-6, 6-2, 7-5.

Overcoming Conchita Martínez, Monica Seles and Lindsay Davenport Within Days of Each Other to Make Maiden Grand Slam Final

In the fourth round, Serena would meet the experienced and crafty Conchita Martínez. After the first set, Williams found herself in the same position as in her previous match against Clijsters, down a set (4-6). But the young American’s powerful play was too much for the Spaniard in the second set, as Serena leveled the match at one-set all by winning the second set 6-2. Despite Martínez’s best efforts, she was unable to counter Williams’ flat and powerful ground strokes point after point as the 17-year-old American ran away with the final set, winning it 6-2. With a 4-6, 6-2, 6-2 win over 16th seed Conchita Martínez, Serena Williams was into her maiden Grand Slam quarterfinal.

In the quarterfinals, Serena Williams would face a more stern test in fourth-seeded Monica Seles. In a hard hitting battle from the back of the court, both women were hitting with incredible length as well as power. In the first set, Seles edged Williams to win it 6-4. Serena had been in this position before in her last two matches and she knew exactly what to do to fight back. With some big serving and hitting, Williams fought back to win the second set, 6-3, much to the delight of a nearly packed Arthur Ashe Stadium under the lights.

Towards the end of the second set until the end of the match, the 17-year-old Serena showed tremendous grit, resilience and tenacity - much like she does today - to overcome Seles. Sealing the win with a big serve down the T that forced Seles to make a return error, Williams had done it again. She defeated her compatriot 4-6, 6-3, 6-2. Coming back after losing the first set in her last three matches, the young American from Compton, California with white beads in her hair, was beginning to make quite a splash in the Big Apple.

In the semifinals, Serena would face number two seed and compatriot Lindsay Davenport. Having met three times before this encounter with Williams leading the head-to-head series 2-1, this was going to be a spectacular match, on paper. On the hard courts of New York City, this WAS a spectacular match. Serena edged Lindsay in the first set, winning it 6-4 before Davenport hit back emphatically, winning it 6-1.

What made this match so interesting was how both women were able to counter the other’s powerful and heavy ground strokes with powerful and heavy strokes of their own. On top of that, both players had fantastic serves that were placed to perfection, time and time again. As a result, neither player was willing to give an advantage to the other. The third set proved to be the most dramatic of the encounter as Williams got a crucial break off of Davenport’s serve to give herself the advantage.

With some great serving from Serena, she managed to hold on to that lead for the rest of the set. Davenport saved a few match points trailing 3-5 on her own serve but it was Serena Williams’ day. Forcing an error off of Lindsay’s backhand, Serena had done it. She defeated the world number 2 6-4, 1-6, 6-4 to advance to her maiden Grand Slam final. No one would have guessed that this was Williams’ maiden Grand Slam semifinal as she had no nerves closing the match out up 5-4 in the final set. The American would face number one and top-seeded Martina Hingis in the final.

The Slam Final That Changed Serena’s Life and Career

In the final, Williams and Hingis would meet for the 6th time of their careers. Martina had the slender 3-2 lead but Serena had won their last meeting which was in Los Angeles, only a few weeks before the Open. With Hingis being the world number one at the time of this final, she was consider the one to beat. On top of that, these two young women had a “war of words” during their respective press conferences because at the beginning of the tournament, Richard Williams predicted that his daughters would meet in the final, a comment that clearly irked Hingis, causing a feud between Martina and the Williams family.

Martina said in a press conference: "They (the Williams sisters and their father Richard) have a big mouth, they always talk a lot so... If it happened before, it’s going to happen again.” Serena responded saying: “She just speaks her mind. I guess it has something to do with not having a formal education.” Even though the two parties apologized to one another and they all had a good laugh about it, you could still sense that Serena wanted to destroy Martina in the final. She had a lot to prove to herself, Hingis, her family and the world.


The young American showed no signs of early nerves in her maiden Grand Slam final as she raced out to an early 3-0 lead on the world number 1 with some tremendous power. Hingis managed to recover the break, while trailing 2-4 in the first set. She had to hold to consolidate the break to level the match at four games all. Williams was not going to let that minor blip affect the rest of her game though.

The 17-year-old was hitting some powerful and clean ground strokes to set up shorter replies from Hingis to attack on. Eventually, it paid off. With Martina unable to counter the brutal hitting from Serena, the American broke serve again to go up a 5-3 lead. Hingis managed to push the next game to deuce but some great serves from Williams got herself out of trouble as she took the opening set, 6-3. To show you how aggressive Williams was off the ground, Martina only hit one winner in that set to Serena’s 19.

In the second set, it was a much tighter affair as Hingis was beginning to maneuver the ball around the court to send Serena running from side-to-side. The world number one was also stepping in to take more shots on the rise, to stop the American from dictating most of the points. Williams continued to be aggressive and as a result, both women were pushing each other to raise their level higher and higher.

At 2-all in the second set, Serena sensed her opportunity to break was coming and when it came, she took it at the second time of asking, to go up a set and 3-2 on the world number one. Up 5-3 now, Serena was ready to win the title, to become the first African American woman to win the U.S. Open since Althea Gibson did it in 1957 and 1958. However, when two of her championship point opportunities were there to be taken, the 17-year-old began to get tight, making two backhand unforced errors on those two match points. In the next game, the momentum was quickly shifting onto Hingis’ side. Williams, who had been dominant on serve all afternoon and early evening, was beginning to cave under the pressure.

The world number one did what she did best - counterpunch. Hingis just kept a few extra balls in play to prolong the rallies and soon enough, Williams began to misfire and lose her composure. The 18-year-old Swiss managed to get the break back and to eventually, push the match into a second set tiebreak. Would Serena be able to rebound from her two missed opportunities?

In the tiebreak, both women were pushing each other beyond their limits. The crowd was going crazy after every point, no matter who had won it. With Serena being on the offense and Martina being on the defence for most of the tiebreak, the rallies became longer and longer. Everyone watching was holding their breath while watching these two incredible women battle it out in front of their eyes. At 4-all in the tiebreak, Serena went for broke on a second serve return and it paid off. She was now up 5-4 in the tiebreak.

Two big serves and the 1999 U.S. Open title would be hers. On the next point, Williams was trying to maneuver the ball from side-to-side but Hingis’ anticipation helped the Swiss Miss get every ball back. At the end of the rally, Serena found herself at the net and Martina attempted to hit a topspin lob over her. Unfortunately for Hingis, it landed out. Williams was pumped. She now had two more championship points. On her third chance to win the title, Martina hit a backhand that landed out and Serena had done it. Serena Williams had won her maiden Grand Slam title with a 6-3, 7-6(4) win over Martina Hingis.

Photo credit: Getty Images

In a state of utter disbelief, Serena put her hand on her chest and said “Oh my god! Oh my god!” over and over again. She looked around the sold out Arthur Ashe Stadium to see everyone give her a standing ovation. Moments later, Serena stood on a chair to get into the stands to hug her and kiss her mother, Oracene Price and father, Richard Williams. Both of them made so many sacrifices to give Serena the life she had always wanted and it all paid off. Richard Williams in particular, after teaching himself how to play tennis, to teaching his daughters Serena and Venus Williams, had done the unthinkable.

When he predicted that his daughters would both be world number one and they would both win a Grand Slam title, many people laughed at the thought. But now, he had proven every doubter wrong and he could not be more proud of his daughter. In an interview with the media after the match, he said: “This is my proudest moment. Words cannot describe how I’m feeling.”

Serena Williams would go on to win twenty more grand slam titles after that historic night and she’s still going. With someone who still has such a burning passion for something she has already achieved so much in, there is no telling what she could do in the next few years of her illustrious career.

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About the author
Max Gao
Max Gao is a sports writer specializing in tennis and the Toronto Blue Jays, who has also written on the Rogers Cup website as a guest contributor in the past.