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|Vasek played his first tournament at age 6, competing at the under-12 level and still emerging as the champion.
Initially playing USTA at the age of 7, Vasek won his first 12-and-under tournament. He continued to beat high-ranked and respected players such as Ryan Farber. Pospisil reached the doubles final of his first junior International Tennis Federation event, the 2005 Canadian U18 ITF World Ranking event, with compatriot Graeme Kassautzki. He and Kassautzki won the doubles event. Partnering another star junior Canadian, Milos Raonic, Pospisil won his second doubles title in December 2006, the Prince Cup in the United States. He also won back-to-back doubles titles in the Czech Republic in January and February 2007, as well as the Guru Cup in Italy in May.
In singles, Pospisil won the ITF Flevoland Junior Championships in the Netherlands in February, the 25th All-Canadian ITF Junior Championships in April, and the Canadian U18 ITF World Ranking Event, the last one without losing more than four games in any set.
Pospisil won two more European events that summer in doubles and was finalist three more times. He capped his summer off by reaching the 2007 U.S. Open boys' doubles final, partnering Grigor Dimitrov. The pair lost to Jonathan Eysseric and Jérôme Inzerillo. In December, he and partner Roman Jebavý won the doubles event at the prestigious Dunlop Orange Bowl.
In March 2007, Pospisil won his first professional tour tournament singles match, at the Canada F1 Futures event, defeating Guatemalan No. 1 Christian Paiz. In the second round, he lost to compatriot Rob Steckley in straight sets. Two weeks later at the Canada F3, he captured his first career title, in doubles, partnering compatriot Érik Chvojka. In June 2007, he and Chvojka lost in the first round of the UniCredit Czech Open, which was Pospisil's first ATP Challenger event.
In November 2008, he won the Challenger Banque Nationale de Rimouski doubles title with compatriot Milos Raonic and two more ITF Futures doubles titles.
In May 2009, Pospisil and partner Adil Shamasdin won the Mexico F4 and F5 doubles titles, as the tournament top seeds. In July 2009 at the USA F17 in Peoria, Illinois, Pospisil reached his first professional singles final, losing to Michael Venus. In doubles, he and Raonic, again the top seeds, won the title, defeating Matt Reid and Dennis Zivkovic in the finals. In August 2009, Pospisil lost in singles in the first round of qualifying for the Rogers Cup to fifth seed Jan Hernych. The following week, he and partner Marius Copil, the top seeds, took the title of the Romania F14 without dropping a set. In September 2009 at the Italy F28, he and partner Marcus Willis, the top seeds, took the title. The following week, Vasek captured the singles title of Italy F29, his first singles title, defeating third seed Francesco Piccari in the final. Two weeks later, Pospisil was in top form, capturing his second title in singles in as many tournaments, Italy F30, and without dropping a set or even reaching a tie-break. He was the seventh seed, and in the final he beat second seed Matteo Viola. After being off for three weeks, Pospisil, as second seed in singles, won Mexico F12, again without dropping a set. In doubles, he and partner Nima Roshan of Australia, the third seeds, also took the tournament title. The following week, Vasek won Mexico F14 as third seed in singles, saving his best tennis for the latter rounds, as he defeated sixth seed Daniel Garza in the semifinals and fifth seed César Ramírez in the final. This was Pospisil's fourth consecutive title and third without dropping a set. Two weeks later, Pospisil, the top seed, lost at Mexico F15 in the semifinals. This loss snapped his 23-match winning streak. After a week off, Pospisil and his partner Adil Shamasdin won the doubles title at the Challenger Britania Zavaleta.
In mid-March 2010, Pospisil was the top seed in singles at the Canada F3 in Sherbrooke. He lost only one set in capturing his fifth ITF tour title, defeating Raonic, the second seed, in the final, in three sets. In the second week of April 2010, Pospisil won the doubles title of the Abierto Internacional del Bicentenario Leon, partnering Santiago González as the top-seeded pair. In August 2010, Pospisil lost in the first round of qualifying for the Rogers Cup to eventual qualifier Illya Marchenko. He played doubles in the main draw as a wild card, partnering Raonic. Together, in the first round, they became, and remain, the only team to ever defeat the doubles team of Rafael Nadal and Novak Djokovic. This was his first win in an ATP Tour main draw event. After two weeks off, he, as the tournament top seed, took the singles title at the ITF Mexico F6, defeating fifth seed David Rice in the final. Pospisil won a second consecutive singles title, Mexico F7, by defeating second seed Adam El Mihdawy in the final. In October 2010, Pospisil again was the top seed in singles at Canada F5 in Markham, Ontario and captured the title, defeating fifth seed Nicholas Monroe in the final. It was the eighth Futures singles title of his career.
At the midway point of 2011, Pospisil captured three Challenger doubles titles and two Futures titles, including one in singles. In March at the Rimouski Challenger, he won the doubles title partnering Treat Conrad Huey. Two weeks later, Pospisil captured the doubles title of USA F8 partnering Nicholas Monroe. Two weeks later, in April, he won his third straight doubles title, the 2011 Tallahassee Tennis Challenger playing with Bobby Reynolds. In May 2011, Pospisil won his ninth career ITF Futures singles title, Korea F2. In June 2011 at Wimbledon, attempting to qualify for a Grand Slam tournament for the first time, Pospisil lost in the second round. The following week, he teamed with Reynolds, as the second seeds, to capture the title of the Jalisco Open. In September 2011, Pospisil was instrumental in seeing the Canadian Davis Cup team come back from two rubbers down to win a Davis Cup tie, for the first time. The win allowed the team to face Israel, in September, in a World Group play-off. Missing through injury their two top singles players, Milos Raonic and Frank Dancevic, Pospisil played No. 1 singles and doubles. He lost his first rubber in four sets, to Iván Endara. With fellow British Columbian Philip Bester also losing, Pospisil and veteran doubles specialist Daniel Nestor had to win their doubles match to keep the tie alive, and did, in three close sets. Perhaps buoyed by this win, Pospisil looked like a new player in beating Júlio César Campozano comfortably. Bester then won the tie-deciding rubber, also in straight sets. In July 2011, Pospisil won his tenth ITF Men's Circuit singles title in Saskatoon, without dropping a set. In August 2011, Pospisil upset world No. 22 Juan Ignacio Chela in the first round of the 2011 Rogers Cup, but lost in the second round to third seed Roger Federer. In doubles, he and partner Adil Shamasdin lost in the first round. He also reached the second round of the 2011 US Open where he was defeated by Feliciano López.
In January 2012, Pospisil qualified for the Aircel Chennai Open and lost in the first round of the main draw to Andreas Beck. He won his first ATP Challenger title in March 2012, defeating Maxime Authom. After this win, he entered the world's top 100 for the first time. His second Challenger title (Granby, Canada) followed in July 2012, lifting Pospisil to world No. 85. At the 2012 Summer Olympics, he lost to David Ferrer in the first round of singles play and reached the second round in doubles with Daniel Nestor. He reached the second round of the 2012 Rogers Cup for the second straight year after upsetting world No. 26 Andreas Seppi. He lost to world No. 10 Juan Mónaco in the next round.
Pospisil had to skip all tournaments in early 2013, including the Australian Open, due to mononucleosis. After recovery, he contributed to Canada's Davis Cup success by winning the doubles match against Italy with Daniel Nestor in April. At the beginning of May, he won his third ATP Challenger singles title and biggest to date when Michał Przysiężny retired in the third set in Johannesburg. Pospisil reached his first ATP semifinal in July at the Claro Open Colombia in Bogotá, but lost to local Alejandro Falla. At the beginning of August, Pospisil won his second ATP Challenger of the year at the Odlum Brown Vancouver Open, where he defeated Daniel Evans in the final.
He entered the Rogers Cup in Montréal as a wild card. In the first round against world No. 20 John Isner, he lost the first set, 5–7, but then won two tiebreaks to take the match. He followed this with a straight-set victory over Radek Stepanek, and then surprised world No. 6 Tomáš Berdych by upsetting him 7–6(7–5) in the third-set tiebreaker to reach the quarterfinals. This was Pospisil's first top-10 win. In the quarterfinals leading 3–0 in the first set, Pospisil's opponent Nikolay Davydenko retired due to illness, thus making Pospisil a semifinalist. In the semifinals, he lost to compatriot Milos Raonic after a third-set tiebreak. With this result, Pospisil was ranked in the top 40 for the first time in his career.
In Cincinnati, he defeated world No. 17 Gilles Simon in the first round, but succumbed to Belgian David Goffin in the second round. At the US Open, he lost in the first round to Brazilian Rogério Dutra Silva. In doubles, he and Daniel Nestor made it to the third round, where they were defeated by the Bryan brothers.
In Davis Cup action against Serbia, he lost both of his singles rubbers against Novak Djokovic and Janko Tipsarevic, but won his doubles rubber, partnering Daniel Nestor. In October at the Masters 1000 in Shanghai, Pospisil beat his second top-10 player when he defeated world No. 10 Richard Gasquet in the first round. He lost to Gaël Monfils in the next round. He reached the semifinals of the Swiss Indoors but was defeated by world No. 6 Roger Federer.
Pospisil began the year strongly by reaching the semifinals of the Aircel Chennai Open. He withdrew from his third round match at the Australian Open, where he was scheduled to play eventual champion Stanislas Wawrinka, due to a back injury. He made a return at the Abierto Mexicano Telcel, but lost to Alexandr Dolgopolov in the first round. He then lost his second-round match at the BNP Paribas Open to Mikhail Kukushkin. Pospisil began his clay-court season at Monte Carlo, but lost in the first round to Roberto Bautista Agut in straight sets.
At Wimbledon, Pospisil lost in the first round of singles, losing to Robin Haase, but partnering American Jack Sock, he won the men's doubles title, defeating the eighth, second, and fifth seeds en route to the final, where they defeated the defending champions the Bryan brothers in five sets. Pospisil and Sock won their second straight doubles title with a victory over Steve Johnson and Sam Querrey at the BB&T Atlanta Open. Pospisil reached his first ATP singles final at the Citi Open a week later with wins over Rajeev Ram, world No. 5 Tomáš Berdych, Santiago Giraldo and world No. 14 Richard Gasquet. He was defeated by world No. 7 Milos Raonic in the first all-Canadian final in ATP history.
Pospisil and Sock reached their third straight final at the Cincinnati Masters, but were defeated by the Bryan brothers in straight sets, ending their record winning streak for a debut team at 14. In October at the China Open, he reached the doubles final with Julien Benneteau, but the duo was defeated in three sets by Jean-Julien Rojer and Horia Tecău. At the end of the month, Pospisil won his third doubles title of the season at the Swiss Indoors with Nenad Zimonjić.
Pospisil started his 2015 season at the Hopman Cup, representing Canada with Eugenie Bouchard. He won his three singles matches, but Canada finished third in their group and was eliminated from the competition. A week later, Pospisil entered the Apia International, losing to fourth seed Julien Benneteau in straight sets in the second round.
At the Australian Open, Pospisil reached the third round for the second straight year, but lost to Guillermo García-López in straight sets. In doubles, Pospisil and partner Julian Knowle advanced to the second round; however, they had to retire from this match.
At Indian Wells in March, Pospisil and Sock won their third doubles title together, and their first Masters 1000, after defeating Simone Bolelli and Fabio Fognini. At the Miami Open a week later, Pospisil and Sock reached their second consecutive Masters 1000 final, but lost to the Bryan brothers. Following this tournament, Pospisil's world doubles ranking rose to No. 5, and in doing so, he became the first Canadian in approximately 14 years to overtake Daniel Nestor as the country's top-ranked doubles player.
At Wimbledon, Pospisil reached the quarterfinals of a Grand Slam for the first time in his singles career. Pospisil beat French qualifier Vincent Millot, 30th seed Fabio Fognini, local wildcard James Ward, and 22nd seed Viktor Troicki. All matches extended to five sets except the one against Fognini. He was defeated in the quarterfinals by world No. 3 Andy Murray in straight sets. In doubles, Pospisil, who was the defending champion with his American partner Jack Sock, lost to the 13th seeded and eventual runners-up Jamie Murray and John Peers in the third round.
At the China Open in October, Pospisil won his second doubles title of the season when he defeated, with Sock, fellow Canadian Daniel Nestor and Édouard Roger-Vasselin in the final. The next week, Pospisil reached the second round of the Shanghai Masters, losing to 11th seed Richard Gasquet in three sets. In doubles, Pospisil and Sock were knocked out in the first round by the Australian pair of Nick Kyrgios and Bernard Tomic. At his last tournament of the year, the Valencia Open, Pospisil reached the semifinals, where he lost to João Sousa.
Pospisil started his 2016 season at the Chennai Open as the seventh seed, but was defeated by Aljaž Bedene in the first round. A week later at the Auckland Open, he won his first match of the year against seventh seed Ivo Karlović, before falling to doubles partner Sock in straight sets in the next round. At the Australian Open, he lost his first-round match to world No. 15 Gilles Simon in four sets. At the Rotterdam Open in February, Pospisil won the sixth doubles title of his career, his first with Nicolas Mahut. At the Indian Wells Masters in March, Pospisil reached the second round in singles and the final in doubles.
In May at the Rome Masters, Pospisil was defeated in the opening round in singles and finished runner-up in doubles with Sock. At the French Open, he lost in the first round in singles and in the second round in doubles. At Wimbledon, Pospisil was again defeated in the first round, this time to Albert Ramos-Viñolas in four sets. He reached the third round of the doubles event. At the Rogers Cup, Pospisil beat Jérémy Chardy in the opening round but lost to Gaël Monfils in the next round. At the Olympics, he lost in the opening round in singles once again to Monfils and in the bronze medal match in doubles with Daniel Nestor. In September, Pospisil advanced to the second round of the US Open in singles. At the Shanghai Rolex Masters in October, he reached the third round in singles of a Masters 1000 for the second time of his career, defeating respectively world No. 20 Ivo Karlović and world No. 18 Grigor Dimitrov.
During the offseason, Pospisil hired Hall of Famer Mark Woodforde to be his new coach. At his first tournament in 2017, the Qatar ExxonMobil Open, he reached the doubles final with Radek Štěpánek. In February, he won his two singles matches at the Davis Cup World Group over top 50 players Kyle Edmund and Dan Evans. The next week at the ATP Challenger 100K in San Francisco, Pospisil made it to the singles final where he was defeated by Zhang Ze in three sets. At the Masters 1000 BNP Paribas Open in March, Pospisil qualified for the main draw and defeated Lu Yen-hsun in the opening round. In the second round, he upset world No. 1 Andy Murray in straight sets, his first win over a top-10 player since 2014. He lost to fellow qualifier Dušan Lajović in the next round. In May, Pospisil won his fifth ATP Challenger singles title in straight sets over Go Soeda at the 150K in Busan. In June at the Ricoh Open, he advanced to his first ATP quarterfinal of the season but was defeated by world No. 7 Marin Čilić.
Pospisil won in January 2018 the sixth ATP Challenger of his career with a victory over Ričardas Berankis at the Open de Rennes. In February, he won his second ATP Challenger title of the season after defeating Nicola Kuhn in the final in Budapest. In May, he advanced to his third ATP Challenger final of the season, losing to Yoshihito Nishioka in Gimcheon. The next week, Pospisil reached the final in Busan for the second straight year, but was not able to defend his title with a loss to Matthew Ebden.
Then he injured his back during a second-round qualifying match at the Paris Masters in October and had a successful surgery on his back in New York City in January 2019 to repair a herniated disc. He was ready to return from a back injury for 2019 Wimbledon.
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