Williams was born in Lynwood, California, to Richard Williams and Oracene Price. Her talents were apparent at the age of seven when a professional local tennis player named Tony Chesta spotted Williams and quickly identified the talent. The Williams family moved from Compton, California, to West Palm Beach, Florida, when she was ten, so that Venus and Serena could attend the tennis academy of Rick Macci, who took notice of the sisters and who would provide additional coaching. He did not always agree with Williams's father but respected that "he treated his daughters like kids, allowed them to be little girls".

Williams started the 1999 tour in Australia, where she lost to No. 10 Steffi Graf in the quarterfinals of the Medibank International in Sydney and No. 1 Davenport in the quarterfinals of the Australian Open. However, she rebounded at the Faber Grand Prix in Hanover, defeating Graf for the first time in the semifinals before losing the final to No. 3 Novotna. Williams then successfully defended her titles in both Oklahoma City and Key Biscayne. She defeated Novotna and Graf to reach the final in Key Biscayne, where she defeated Serena in three sets in the first final on the WTA Tour to be contested by two sisters. Williams played four clay court events during the spring. She lost her first match at the Bausch & Lomb Championships in Amelia Island, Florida. Three weeks later, however, she won her first title on clay at the Betty Barclay Cup in Hamburg, defeating Mary Pierce in the final. Williams then won the Tier I Italian Open in Rome, defeating No. 1 Hingis in the semifinals and No. 8 Pierce in the final. At the French Open, she extended her winning streak to 22 matches before losing in the fourth round to No. 125 Barbara Schwartz. Williams teamed with Serena to win the women's doubles title at this event, the first Grand Slam title the pair won together. At the 1999 Wimbledon Championships, Williams defeated No. 17 Anna Kournikova in the fourth round to reach the quarterfinals for the second consecutive year, where she lost to eventual runner-up Graf. Williams rebounded in the summer when she won two Fed Cup matches against Italy and lost in the final of the Bank of the West Classic in Stanford to No. 1 Davenport. One week later, Williams defeated Davenport in the semifinals of the TIG Tennis Classic in San Diego before losing to No. 2 Hingis in the final. In her last tournament before the US Open, Williams won the Pilot Pen Tennis in New Haven, Connecticut, defeating No. 5 Seles in the semifinals and Davenport in the final. On August 30, 1999, her world ranking reached third for the first time. Seeded third at the US Open, Williams lost in the semifinals to No. 1 Hingis in three sets. However, she teamed with singles champion Serena at this event to win their second Grand Slam women's doubles title. During the remainder of the year, Williams contributed to the USA's victory over Russia in the Fed Cup final, winning one singles rubber before joining Serena to win the doubles rubber. At the Grand Slam Cup in Munich, Williams defeated Hingis in the semifinals before losing to Serena for the first time in the final. Williams won her sixth title of the year at the Tier I event in Zurich, defeating No. 1 Hingis in the final. Four weeks later, she lost to Davenport in the semifinals of the tournament in Philadelphia. Making her debut at the year-ending Chase Championships, Williams lost to Hingis in the semifinals. She finished the year ranked No. 3. CANNOTANSWER

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