Chakvetadze hit her peak of world no. 5 in 2007 after a semifinal appearance at the US Open. Also in that year, she reached the quarterfinals at the Australian Open and the French Open, both of which were career bests for those events. Four of her eight career singles titles also occurred in 2007.
2001–2006: Early career and entering Top 50
In 2003, she made it to the final of the Junior Championships at Wimbledon before falling to Kirsten Flipkens of Belgium 6–4, 3–6, 6–3. The same year, she won the International Bavarian Junior Challenge, defeating Marta Domachowska of Poland 7–6, 6–5. Her record as a junior was 67–19 in singles, and 22–14 in doubles. Her highest world ranking as a junior was #22 achieved in December 2003.
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(3), 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.
2007: Breakthrough year , World No 5
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.
In February, Chakvetadze reached the quarterfinals of the Open Gaz de France in Paris, where she lost to Amélie Mauresmo 7–6(5), 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 Openin 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, 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 championVenus Williams in the quarterfinals 6–7(5), 7–6(3), 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(4). She then lost her semifinal match with Sharapova 6–2, 6–2.
2008: Continued success
At the Australian Open, Chakvetadze lost in the third round to Maria Kirilenko 6–7(6), 6–1, 6–2. She then helped defending champion Russia win its first round tie against Israelin 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(2).
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(0), 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(4). 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.
2009: Out of Top 50
Chakvetadze was seeded 17th at the Australian Open where she lost in the second round to Jelena Dokić 6–4, 6–7(4), 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 defeatedVirginia 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 seededJelena Janković 6–7(5), 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 Tennistournament, 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 compatriotVera 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.
2010: Return to form and injuries
Chakvetadze started the year with a first round loss at the 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 PTT Pattaya Open, Chakvetadze lost to Tamarine Tanasugarn in the quarterfinals.
In March, Chakvetadze competed at the 2010 BNP Paribas Open in Indian Wells, where she retired with an ankle injury in the second round whilst trailing at 6–2, 5–3 toAgnieszka 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 Polsat Warsaw Open where she fell in the qualifying round to Bojana Jovanovski 7–5 7–6(4). 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 advanced to the third round, where she lost 4–6 7–5 6–1 to qualifier Alison Riske. At the Aegon International, Chakvetadze reached the second round of qualifying, where she lost 7–5 4–6 6–2 to Jarmila Groth of Australia. In the first round of Wimbledon, Chakvetadze defeated faced defending champion Serena Williams in the second round and lost 6–0 6–1.
In the GDF Suez Grand Prix, Chakvetadze fell to second seed Alexandra Dulgheru 7–6(5) 1–6 6–2 and at the 2010 ECM Prague Open she fell to Ksenia Pervak in the first round.
At the Banka Koper Slovenia Open in Portorož, Chakvetadze defeated Johanna Larsson 6–1, 6–2 in her first final in two years and to win her eighth WTA Tour title. In the Portorož 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 e-Boks Danish Open in Copenhagen. She lost in the semi-final 6–1, 2–6, 6–4 to top seed Caroline Wozniacki.
Next, Chakvetadze entered the EmblemHealth Open in Bronx to prepare for the US Open. She defeated Sofia Arvidsson 4–6, 6–2, 6–2 in the final to win the second title of the year. At the US Open suffered a loss to Urszula Radwańska in the first round.
Chakvetadze then entered the Tashkent Open in Uzbekistan, where she retired in the htird round against Evgeniya Rodina due to a viral illness. At the 2010 China Open she fell in the final qualifying round to Kateryna Bondarenko. At the 2010 Generali Ladies Linz Chakvetadze lost to Sybille Bammer. At the Kremlin Cup, Chakvetadze lost in the quarter final to Vera Dushevina 6–3 7–6.
Chakvetadze ended 2010 ranked 56. She won one singles title and reached two doubles finals.
2011: Illness and injuries
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. In the 2011 Australian Open Chakvetadze lost in straight sets to Petra Kvitová in the second round.
At the 2011 Dubai Tennis Championships she collapsed due to a viral illness and could not complete the second round match against 1st seed, Caroline Wozniacki after having defeated Daniela Hantuchová 6–1 6–3 in the 1st round. She lost the first set 6–1 and collapsed at 5–3 up when she had a set point. It was later confirmed that Chakvetadze collapsed due to a GI illness that she had been suffering from since before the tournament. As a result, she did not play the Qatar Ladies Open. At the 2011 BNP Paribas Open, she retired against face 24th seed, Maria Kirilenko in the second round down 6–2 1–3. She then missed the 2011 Sony Ericsson Open due to illness.
Chakvetadze returned to competition at 2011 Porsche Tennis Grand Prix. In the first round, she fainted again at 6–1, 5–7, 4–4 against Zuzana Kučová, and retired. Because of these problems, she did not play the 2011 French Open. After a few weeks of hospital testing, Chakvetadze made her return at the 2011 UNICEF Open, where she lost toLourdes Domínguez Lino 6–4, 6–1. Chakvetadze lost to Maria Sharapova 6–2, 6–1 in the first round of the 2011 Wimbledon Championships. Chakvetadze announced that she will not participate in the 2011 US Open because of ankle injury. Chakvetadze ended her year with six wins and eights losses, and ranked outside the top 200.
2012: Continued downfall, out of Top 500
Chakvetadze started the year at the 2012 Moorilla Hobart International where she made it to the quarterfinals, but retired with a leg muscle cramp to 6th seed Shahar Pe’er.
In the first round of the Australian Open, Chakvetadze lost to Jelena Dokic, 6–2, 6–1.
Chakvetadze took a break from the sport for several months before returning to competition in the 2012 e-Boks Open. As a qualifier, she lost in round one to Pauline Parmentier. She also qualified for the 2012 Porsche Tennis Grand Prix, but was beaten by Alizé Cornet.
She failed to qualify for the 2012 Mutua Madrid Open; but managed it at the 2012 Internazionali BNL d’Italia, losing to Sloane Stephens in the first round. At 2012 Brussels Open, she lost in the first round to Yanina Wickmayer.
Chakvetadze returned from injury at the 2012 Citi Open, but lost to Melinda Czink in the opening round. Then, after a string of good wins, Chakvetadze finished runner-up to Romina Oprandi at the 2012 EmblemHealth Bronx Open.
Chakvetadze announced her retirement from professional tennis on September 11, 2013 due to ongoing back problems. Since retiring, Anna has been a tennis commentator for Eurosport.