and world no. 290 Erik 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