Juniors As a junior, Dolgopolov reached as high as No. 21 in the combined world rankings in January 2005. His best showing at a junior major was a quarterfinal at the 2005 French Open Boys' Singles, where he lost against Christian Bak.
2006–2009 Dolgopolov made his
ATP Tour debut in September 2006 at the
BCR Open Romania as a qualifier, losing in the first round to
Christophe Rochus. He was also part of the Ukrainian
Davis Cup team in the tie against Great Britain, where he was defeated by
Andy Murray. Eventually, the younger Dolgopolov decided that he wanted less of his father's influence and develop himself in his own way. In 2009, at age 20, he parted ways with his father and enlisted the help of Australian Jack Reader as his coach. In the quarterfinals, he lost to
Andy Murray, the fifth seed, in four sets. Dolgopolov next hit the clay courts of Latin America. He entered the
2011 Brasil Open in Costa do Sauípe as the fourth seed, receiving a first-round bye. He defeated
Rubén Ramírez Hidalgo in the second round. He then beat
Potito Starace in the quarterfinals and crushed home-town favourite
Ricardo Mello to enter his first ATP tour final. He was defeated by the top seed, world no. 13
Nicolás Almagro in two sets. Dolgopolov then headed to Buenos Aires to play in the
2011 Copa Claro as the seventh seed. He suffered a surprising first-round defeat to Argentinian wildcard
José Acasuso in straight sets. However, partnering
Igor Andreev, Dolgopolov reached his first ATP tour doubles semifinal, but lost to eventual champions
Oliver Marach and
Leonardo Mayer. Dolgopolov then participated in the final leg of the Golden Triangle swing in the
2011 Abierto Mexicano Telcel tournament in Acapulco, as the sixth seed. He defeated Chilean
Paul Capdeville in the first round, and then beat doubles partner
Carlos Berlocq in the second round. He reached the semifinals after beating fourth seed
Stanislas Wawrinka but lost to top seed and world no. 6
David Ferrer in three sets. Dolgopolov next entered the first Masters 1000 series of the year at
Indian Wells, his debut in the tournament. As the 20th seed, he received a first-round bye, and then beat Romanian
Victor Hănescu to reach the third round, where he faced Grand Slam champion
Juan Martín del Potro. He lost the match in straight sets. Dolgopolov was also entered in the doubles tournament. Partnering
Xavier Malisse, they defeated
Tomáš Berdych and
Janko Tipsarević and then shocked top seeds and world no. 1
Mike Bryan and
Bob Bryan. They played
Jamie Murray and
Andy Murray next and defeated the British brothers after being a set down, a break down, and 1–6 down in the super tiebreak. Dolgopolov and Malisse then beat
Rohan Bopanna and
Aisam-ul-Haq Qureshi in the semifinals to enter Dolgopolov's first ATP tour doubles final. They played 2008 Beijing gold medalists
Roger Federer and
Stanislas Wawrinka, and they prevailed in a super tiebreak. Dolgopolov continued his form at the next Masters event, the
2011 Sony Ericsson Open in Miami, reaching the fourth round with wins against Italian
Andreas Seppi and
Jo-Wilfried Tsonga. He then lost to world no. 1
Rafael Nadal in straight sets. Dolgopolov then suffered a disappointing start to the clay season, suffering four consecutive first-round defeats. He was defeated in the first round of the
2011 Monte-Carlo Rolex Masters by
Ernests Gulbis and then lost to
Nikolay Davydenko in the
2011 Barcelona Open Banco Sabadell. He was then beaten by
Santiago Giraldo in the
2011 Mutua Madrid Open and finally by
Potito Starace at the
2011 Internazionali BNL d'Italia. It was later disclosed that he was suffering from pancreatitis since the North American swing, which led him to play sparingly during the early clay season. Dolgopolov managed to regain some of his earlier form in his last clay tournament,
2011 Open de Nice Côte d'Azur, before the
2011 French Open. He beat
Filippo Volandri and
Pere Riba to reach the quarterfinals. There, Dolgopolov pulled off an upset win over top seed
David Ferrer. He lost to
Victor Hănescu in straight sets in the semifinals. Dolgopolov entered the
2011 French Open as the 21st seed. In his first-round match, he played the oldest player in the ATP top 100,
Rainer Schüttler at age 35, and won the match easily. He then beat
Andreas Haider-Maurer comfortably to move into the third round but was beaten by Serbian 15th seed
Viktor Troicki in four sets. Moving to the grass courts of Europe, Dolgopolov's first tournament was the
2011 Gerry Weber Open, seeded seventh, he faced
Robin Haase in the first round and defeated him in three sets before succumbing to
Philipp Kohlschreiber in two sets. Dolgopolov's next tournament was the
2011 Aegon International, where he was seeded second. He lost to
Carlos Berlocq in straight sets. His dismal grass-court season continued into
Wimbledon 2011, where he was seeded 22nd, with a first-round loss to
Fernando González (who had not played in almost a year prior to a few small tournaments before Wimbledon). Before heading into the US Open series of hard-court tournaments, Dolgopolov returned to his beloved clay to play
2011 International German Open in Hamburg. Seeded tenth, he received a first-round bye, and then lost to Finnish player
Jarkko Nieminen, despite being up two breaks in the third set. Dolgopolov then travelled to Croatia, where he took part in the
2011 ATP Studena Croatia Open, where he was seeded second. Receiving a first-round bye, he beat
Filippo Volandri in the second round, finally winning an opening-round match after suffering four consecutive opening-round exits. In the quarterfinals, he beat
Albert Ramos to set up a semifinal meeting with defending champion and former world no. 1
Juan Carlos Ferrero. There, Dolgopolov pulled off an impressive display to defeat the Grand Slam champion in straight sets. Entering his second final of the year, Dolgopolov played Croatian home-town favourite, former top-10 player and fourth seed
Marin Čilić. Faced with a determined opponent, Dolgopolov needed three sets to beat Čilić and win his first ATP singles title. Dolgopolov entered the
2011 Rogers Cup unseeded, missing out on a seeding as world no. 21 (only the top 16 were seeded). He played Canadian wildcard and world no. 290
Érik Chvojka and was stretched to three sets. He was defeated by seventh seed
Tomáš Berdych in the second round. On 18 April 2011, Dolgopolov reached a career-high ranking of no. 20. Seeded 22nd for the
2011 US Open, Dolgopolov defeated
Frederico Gil,
Flavio Cipolla, and
Ivo Karlović to reach the fourth round, where he faced world no. 1
Novak Djokovic. Dolgopolov took Djokovic to a 28 and a half-minute first-set tiebreak, with Djokovic finally prevailing 16–14. Dolgopolov went on to a three set defeat, ending his US Open campaign.
2012: Highest career ranking, ATP 500 title Seeded 4th for the
2012 Brisbane International tournament, Dolgopolov defeated
Alejandro Falla, Igor Andreev, Radek Štěpánek, and Gilles Simon to make it to the final, where he lost to
Andy Murray. This loss was attributed to fatigue over a previous groin injury in the semifinal victory over Gilles Simon. As a result, he reached a career-high ranking of No. 13 on 16 January 2012. At the
2012 Australian Open he lost in the third round to local hope
Bernard Tomic. At the
Croatia Open Dolgopolov defeated Italian
Fabio Fognini in the second round. Alexandr Dolgopolov won his first ATP 500 at the Citi Open in Washington, D.C. He defeated Tommy Haas in the final.
2013: Wimbledon third round Dolgopolov reached three quarterfinals during the spring, in
Brisbane,
Memphis and
Munich. However he failed to make impact in
Masters 1000 and
Grand Slam tournaments, which caused him to steadily fall in rankings. He gave a stern challenge to World No.7 at the time
Juan Martín del Potro. After a quiet first half of the year Dolgopolov reached the third round of
Wimbledon where he played David Ferrer, leading by two sets to one before eventually being overcome in five sets. In the tournaments after Wimbledon Dolgopolov continued to struggle in finding form from the two previous seasons. Some of the more notable results were beating world No.21
Kevin Anderson in
2013 Rogers Cup and former top 10 player
Janko Tipsarević in
Japan Open (tennis) where he has reached quarterfinals. Best result of the year for Dolgopolov was a semifinal in
2013 Winston-Salem Open, where he lost to
Gaël Monfils.
2014: First Masters 1000 semifinal, return to top 30 Dolgopolov began the year at the
Apia International in Sydney, losing in the quarterfinals to eventual runner-up
Bernard Tomic. That was followed by a second round loss to
Jérémy Chardy at the
Australian Open. After losing in the first round of the
Chile Open in Viña del Mar, Dolgopolov reached the finals at the inaugural
Rio Open in Brazil. He defeated
David Ferrer en route to his first final since 2012, however ultimately lost to world no. 1
Rafael Nadal in straight sets. He continued his good run of form at the
BNP Paribas Open in
Indian Wells. He beat Nadal in the third round,
Fabio Fognini in round of 16 and
Milos Raonic in quarter-finals, then lost to
Roger Federer in semifinals. It was the first time he has made it beyond the third round of a Masters 1000 tournament since 2012. At the Miami Open, the Ukrainian defeated
Stan Wawrinka in round of 16 and lost to
Tomáš Berdych in quarter-finals. As a result of his good run of form, Dolgopolov returned to the world's top 30. During the spring clay season, the player won over
Ernest Gulbis in first round of the Monte Carlo Masters, then lost to
Guillermo García López. At the Madrid Masters he defeated
Fabio Fognini, then lost in second round to Gulbis. At the Rome Masters he lost to
Jo-Wilfried Tsonga in first round. At Roland Garros he lost in second round to
Marcel Granollers. Dolgopolov lost to
Grigor Dimitrov in Queen's quarter-finals and Wimbledon round of 32.
2015: Second Masters 1000 semifinal In 2015, Dolgopolov lost in first round of the Australian Open to
Paolo Lorenzi. At the Mexican Open he lost to
Kei Nishikori in quarter-finals. At the Indian Wells Ukrainian he defeated
Santiago Giraldo to reach third round, where he lost to
Milos Raonic. At the Miami Masters the Ukrainian reached round of 16 after winning over
Tommy Robredo, then fell to
Novak Djokovic. In the spring clay season, Dolgopolov lost to Monfils in second round of the Monte-Carlo Masters. At the Rome Masters, he won over
Martin Kližan to reach round of 32, where he was defeated by
Guillermo García López. At Roland Garros he lost in first round to
Nicolás Almagro. In the grass season, the Ukrainian lost to Kohlschreiber in first round of Stuttgart. At Queen's he defeated
Rafael Nadal in first round, then lost to García López in second round. At Nottingham he claimed wins over
Donald Young,
Pablo Andújar,
Dominic Thiem and
Yen-Hsun Lu, then lost in semifinals to
Sam Querrey. At the Wimbledon Championships, the player fell in second round to
Ivo Karlović. In the North American summer tour, Dolgopolov defeated Karlovich to reach round of 16 at Washington, after which he lost to
Alexander Zverev. At the Canada Masters he lost in first round to
Grigor Dimitrov. In Cincinnati he qualified for the main draw by defeating
James Ward and
Santiago Giraldo, then earned a first round bye due to
Kei Nishikori's withdrawal and won over
Bernard Tomic,
Jerzy Janowicz and
Tomáš Berdych to reach the semi-finals, where he lost to world nº 1
Novak Djokovic in three sets, having won the first.
2016–2017: Hopman Cup finalist, third ATP title, US Open fourth round Dolgopolov represented Ukraine alongside
Elina Svitolina at the
2016 Hopman Cup. He won his singles matches against
Jack Sock,
Jiří Veselý and
Lleyton Hewitt. He and Svitolina were the winners of their group in the round robin phase, and went into the final against the Australia Green team. Dolgopolov lost to
Nick Kyrgios 3–6, 4–6. The Ukrainian team were the runners-up of the tournament. Dolgopolov then entered
2016 Wimbledon Championships where he beat Russian
Evgeny Donskoy in 4 tight sets to set up a second round match against
Daniel Evans which he lost in 3 sets. He then entered the
2016 Citi Open and was seed 11, which meant he received a bye for the first round, in the second round match he faced Australian youngster
Jordan Thompson, in the third round he lost in straight sets to
Sam Querrey. Dolgopolov then proceeded to enter the
2016 Rogers Cup, where he lost to
Donald Young in straight sets in the first round. Dolgopolov won his third ATP title at the
2017 Argentina Open defeating top seeded Japanese player
Kei Nishikori. He reached the fourth round of the
2017 US Open (tennis) where he was defeated by top seed World No. 1 and eventual champion
Rafael Nadal.
2018: Australian Open third round Having gotten to the third round of the
2018 Australian Open for the third time in his career, Dolgopolov was defeated by
Diego Schwartzman.
2021: Retirement Dolgopolov announced his retirement on 1 May 2021, having played
Novak Djokovic in his final match on 14 May 2018 at the Internazionali BNL d'Italia in Rome. == Military service ==