Chakvetadze debuted on the ITF circuit in November 2001, losing in the first round in Minsk, Belarus. In July 2002, she won her first ITF doubles title in Istanbul, teaming with fellow Russian Irina Kotkina. At the 2004 U.S. Open, Chakvetadze won three qualifying matchers to reach the main draw of her first Grand Slam singles tournament. In the second round, she defeated World No. 3 Anastasia Myskina 7–6, 6–3 before losing in the third round to Eleni Daniilidou. With this result, she became tied for the second fastest player to defeat a world top 10 in WTA history, tying Serena Williams. She broke into the top 100 in the WTA rankings on September 13, reaching World No. 91. She reached the top 50 on June 6, 2005, coming in at World No. 44. On September 25, 2006, Chakvetadze won her first WTA singles tournament at the Tier III event in Guangzhou, China, defeating Spain's Anabel Medina Garrigues in the final. Two weeks later, she won her second WTA tournament at the Tier I Kremlin Cup in Moscow even though she was unseeded, beating Elena Dementieva and Nadia Petrova en route to the title. These wins helped boost her ranking to World No. 16. Chakvetadze started the year by winning the Tier IV Moorilla Hobart International in Australia, her third WTA tournament title. She defeated fellow Russian Vasilisa Bardina in the final. At the Australian Open, where she was seeded twelfth, she defeated eight-seeded Patty Schnyder in the fourth round before losing in the quarterfinals to top-seeded Maria Sharapova 7–6(5), 7–5.
Video from Anna Chakvetadze
In February, Chakvetadze reached the quarterfinals of the Open Gaz de France in Paris, where she lost to Amélie Mauresmo 7–6, 7–5. She then competed at the Proximus Diamond Games in Antwerp, where she lost in the semifinals to Mauresmo 6–3, 3–6, 6–2. On February 19, she made her top 10 debut on the WTA rankings, at World No. 10. At the Tier I Pacific Life Open in Indian Wells, California, she lost in the fourth round to Shahar Pe'er 6–4, 7–6. She then reached the semifinals of the Tier I Sony Ericsson Open in Key Biscayne, Florida, where she was defeated by World No. 1 Justine Henin 6–2, 6–3. Chakvetadze then played four tournaments in Europe on red clay courts. Chakvetadze lost in the quarterfinals of the Tier II J&S Cup in Warsaw to Jelena Janković, the second round of the Tier I Qatar Telecom German Open in Berlin, and the second round of the Tier I Internazionali BNL d'Italia in Rome. At the French Open, Chakvetadze lost to second-seeded Sharapova in the quarterfinals.
Chakvetadze won her second title of the year, and first grass court title, in 's-Hertogenbosch, with wins over Daniela Hantuchová and Janković. At Wimbledon, however, she was defeated in the third round by 31st-seeded Michaëlla Krajicek in three sets. Chakvetadze then played five tournaments during the North American summer hard court season. At the Tier III Western & Southern Financial Group Women's Open in Cincinnati, Ohio, Chakvetadze was the top-seed and won the title, defeating Akiko Morigami in the final. Chakvetadze won her second consecutive tournament the following week at the Bank of the West Classic in Palo Alto, California, the first tournament of the US Open Series. She defeated Sania Mirza in the final. That was her ninth consecutive match victory and resulted in her ranking rising to World No. 6. At the Acura Classic tournament in San Diego, her 12-match winning streak ended when she lost in the semifinals to top seeded Sharapova for the third time this year 6–3, 6–2 after Chakvetadze had defeated reigning Wimbledon champion Venus Williams in the semifinals 6–7, 7–6, 6–2. Two weeks later at the Tier I Rogers Cup in Toronto, Chakvetadze retired from her second round match after losing the first set to Virginie Razzano. At the US Open, Chakvetadze was the sixth seed and reached the semifinals of a Grand Slam tournament for the first time, losing to Svetlana Kuznetsova 3–6, 6–1, 6–1. This result caused her ranking to rise to a career high of World No. 5. Chakvetadze was the defending champion at the Kremlin Cup in Moscow, but lost her second round match to Dinara Safina 7–6, 6–2. Chakvetadze became the sixth player in 2007 to qualify for the year-ending Sony Ericsson Championships. She reached the semifinals of that tournament by winning two of her three round robin matches, defeating Serena Williams and Janković before losing to Henin 6–1, 7–6. She then lost her semifinal match with Sharapova 6–2, 6–2.
At the Australian Open, Chakvetadze lost in the third round to Maria Kirilenko 6–7, 6–1, 6–2. She then helped defending champion Russia win its first round tie against Israel in the Fed Cup by defeating Tzipora Obziler 6–4, 6–2. Chakvetadze was the top-seed at the Tier II Open Gaz de France in Paris. She defeated Amélie Mauresmo in the quarterfinals, Marion Bartoli in the semifinals, and Ágnes Szávay in the final to win her seventh career singles title. She is now 7–0 in tournament finals. At the Tier I Sony Ericsson Open in Key Biscayne, Florida, Chakvetadze lost in the third round to Sabine Lisicki. At the French Open, sixth-seeded Chakvetadze lost in the second round to Kaia Kanepi 6–4, 7–6. Chakvetadze was seeded eighth at Wimbledon. She defeated Stéphanie Dubois in the first round 2–6, 6–1, 8–6 after Chakvetadze saved two match points at 5–3 and an additional match point at 5–4 in the third set. Chakvetadze won her second and third round matches in straight sets but lost in the fourth round to eighteenth-seeded Nicole Vaidišová 4–6, 7–6, 6–3. Chakvetadze played five tournaments during the North American summer hard court season. She was the second seeded player and defending champion at the Tier II Bank of the West Classic on the campus of Stanford University in California. She lost, however, to Bartoli in the quarterfinals 6–3, 6–4. The following week, she lost in the third round of the East West Bank Classic in Los Angeles to Sybille Bammer. Seeded sixth at the Tier I Rogers Cup in Montreal, Chakvetadze lost in the third round to tenth-seeded Bartoli 4–6, 7–5, 7–6. She then lost in the final of the Pilot Pen Tennis tournament in New Haven, Connecticut to Caroline Wozniacki. Chakvetadze was seeded tenth at the US Open but lost in the first round to Ekaterina Makarova.
Chakvetadze was seeded 17th at the Australian Open where she lost in the second round to Jelena Dokić 6–4, 6–7, 6–3. She also lost the opening round of the Barclays Dubai Tennis Championships to Ayumi Morita. At the Rome Masters, Chakvetadze lost a close three setter to Venus Williams in the third round. At the Madrid Masters, she defeated Virginia Ruano-Pascual in the first round. She then defeated Samantha Stosur in the second round, coming back from 4–1 down in the third set. She fell to Alona Bondarenko in the third round. Chakvetadze, who was seeded 26th at the French Open, suffered a first-round loss to Mariana Duque Marino in three sets 6–3, 4–6, 4–6, thus continuing her disastrous run. In the grass court season, Chakvetadze was able to raise her game in the first round in Eastbourne, where she defeated a third seeded Jelena Janković 6–7, 6–3, 6–2. She lost to Marion Bartoli in the second round. Chakvetadze was seeded 32nd at the 2009 Wimbledon Championships. She lost to Sabine Lisicki in the first round 4–6, 7–6, 6–2, meaning she was out of the top 50 for the first time in quite a while. Chakvetadze began her 2009 US Open Series campaign at the Bank of the West Classic in Stanford, where she was unseeded. She was defeated in the first round by Maria Kirilenko 4–6, 7–5, 6–7. The following week, at the LA Women's Tennis Championships, she won her first two matches, against Virginie Razzano and Alisa Kleybanova, but then lost convincingly to Agnieszka Radwańska 6–3, 6–2 in the third round. Having won the Western & Southern Financial Group Women's Open in Cincinnati in 2007, Chakvetadze went into the 2009 tournament unseeded, and suffered another early round loss to 9th seed Victoria Azarenka in straight sets.
At the Rogers Cup in Toronto she lost again in the first round, to Sybille Bammer 3–6 6–4 6–1, after leading 6–3 4–1. Her next tournament was the Pilot Pen Tennis tournament, in New Haven, where she had been a finalist in 2008. She reached her first quarter-final of the year, defeating Nadia Petrova and Sybille Bammer all in three sets. She then lost to her good friend Elena Vesnina 6–1 7–5. Chakvetadze entered the US Open as an unseeded player for the first time since 2005. She defeated Yurika Sema 4–6 6–1 6–2, but then fell in the second round to compatriot Vera Zvonareva 3–6 6–1 6–1. At her home tournament in Moscow Kremlin Cup she again lost in the first round, to Alona Bondarenko 6–4 6–3. She ended 2009 at number 69, her lowest in 5 years. Chakvetadze started the year with a first round loss at the 2010 ASB Classic in Auckland to wildcard Kimiko Date Krumm, 6–1, 6–2. At the Australian Open, she was defeated in the first round by 12th-seed Flavia Pennetta, 6–3, 3–6, 6–2.At the 2010 PTT Pattaya Open, Chakvetadze defeated Jill Craybas in the first round and defeated Anastasia Rodionova in the second. She fell to Tamarine Tanasugarn in the quarterfinals. In March, Chakvetadze competed at the 2010 BNP Paribas Open in Indian Wells, where she had a 2–6, 6–3, 6–1 win over Anne Keothavong. In the second round, she retired with an ankle injury whilst trailing at 6–2, 5–3 to Agnieszka Radwańska. At the Sony Ericsson Open in Miami, Chakvetadze had a first round loss to Kimiko Date Krumm 7–5, 3–6, 6–4. Her next tournament was 2010 Polsat Warsaw Open where she fell in the qualifying round to Bojana Jovanovski 7–5 7–6. At the 2010 French Open, she was two points away from winning the match in straight sets, before losing in the first round to Angelique Kerber 5–7 7–6 6–4. During the grass court season, in the 2010 AEGON Classic she defeated Melanie South 3-6 6-4 6-4 and 8th seed Andrea Petkovic 6-4 6-4 to advance to the third round, where she lost 4-6 7-5 6-1 to qualifier Alison Riske. At the 2010 AEGON International, Chakvetadze won her first match in qualifying over Anna Lapushchenkova of Russia 6-1 6-1. In the 2nd round of qualifying, Anna lost 7-5 4-6 6-2 to Jarmila Groth of Australia. In the first round of Wimbledon, Chakvetadze defeated Andrea Petkovic of Germany 3-6 6-4 6-4 in one hour and 52 minutes. She faced defending champion Serena Williams in the second round and lost 6-0 6-1.
n the 2010 GDF SUEZ Grand Prix, Chakvetadze fell to second seed Alexandra Dulgheru 7-6 1-6 6-2 and at the 2010 ECM Prague Open she fell to Ksenia Pervak in the very first round. At the 2010 Banka Koper Slovenia Open in Portoroz, Chakvetadze reached the quarterfinals by defeating Ekaterina Makarova 6-4, 6-1 and defending finalist Sara Errani 6-1, 6-2. In the quarterfinals she defeated No.6 seed Vera Dushevina in a match lasting over two hours, saving two match points in the final set at 4-5 before finally winning 2-6, 6-3, 7-5. In the semifinals, Chakvetadze beat 7th seed Polona Hercog 0-6, 6-2, 6-2. She defeated Johanna Larsson 6-1, 6-2 in her first final in two years and to win her eighth WTA Tour title. Her ranking is set to rise to top 80 in the world as a result. In the Portoroz doubles final, Chakvetadze and Marina Erakovic, lost to Kondratieva-Uhlířová after the super tie-break – 6-4, 2-6 and 10-7. Chakvetadze then entered the 2010 E-Boks Danish Open in Copenhagen. She qualified by defeating Karolina Kosińska and Kathrin Woerle. In the main draw she then defeated Johanna Larsson 6-4 7-6 and Anna Lapushchenkova 6-3, 6-4. In the quarterfinals she defeated Polona Hercog 6-4 6-3 to book her place in the semi-final where her winning streak ended with a 6-1, 2-6, 6-4 loss to top seed Caroline Wozniacki. Chakvetadze then decided to enter a 100K ITF tournament in the Bronx to prepare for the US Open. The tournament had a quality field. In the first round Chakvetadze defeated Yung-jan Chan 6-7 6-1 6-3. She then defeated top-seed Lucie Šafářová in the second round, 6-7 6-4 6-4. She then played her quarterfinal and semifinal matches on the same day, defeating sixth-seed Anastasija Sevastova 6-3 4-6 6-4 in the quarters and Ekaterina Makarova 6-3 6-3 in the semis. For the title, she defeated Sofia Arvidsson 4-6 6-2 6-2. At the US Open suffered a surprising loss to Urszula Radwańska. Chakvetadze then entered the 2010 Tashkent Open in Uzbekistan, In the first round Chakvetadze defeated Zuzana Kucova 6-3 7-5, In the second round, she then retired to Evgeniya Rodina due to a viral illness. At the 2010 China Open she qualified by defeating Wanting Lu but fell in the final qualifying round to Kateryna Bondarenko. At the 2010 Generali Ladies Linz Chakvetadze lost to Sybille Bammer. At her favourite tournament 2010 Kremlin Cup, Chakvetadze caused an upset in the first round because she defeated no.3 seed Li Na 6-4 6-2. She defeated Mariya Koryttseva of Ukraine in the second round 6-1 6-2, before losing in the quarter final to Vera Dushevina 6-3 7-6. Anna ended 2010 ranked 56. She won 1 singles title and reached two doubles finals. Chakvetadze started the year with a first round loss at the 2011 Brisbane International to compatriot Ksenia Pervak. She again lost in the first round at the 2011 Moorilla Hobart International, this time to Sara Errani. She will play Olga Govortsova in the first round of the 2011 Australian Open.
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