Grigor Dimitrov

In 2008, Dimitrov began frequent participation in men's events. His first title came on clay at a futures tournament in Barcelona. His first ATP level match was at the Ordina Open where he lost to Igor Andreev in straight sets. After his junior US Open title he won back to back futures tournaments in Madrid on hard court and rose 300 places to career high ranking of 477. The achievement attracted enough attention to earn him a wildcard into the Mutua Madrileña Madrid Open qualifying draw where he lost to then No. 64, Florent Serra of France. After being granted another wildcard to the Davidoff Swiss Indoors qualifying draw and defeated No. 122, Jiří Vaněk, in three sets in the first round for his first ATP level win, before losing to Julian Reister.

In 2009, he was granted a wildcard to the main draw of the ABN AMRO World Tennis Tournament and scored an upset over then world No. 23, Tomáš Berdych, earning his first ATP main draw win. In the second round he faced world No. 1, Rafael Nadal, and lost in three sets. He was granted a wildcard to the main draw of the Open 13, but lost to world No. 8, Gilles Simon, in the first round, despite serving for the match at ninth game of the third set. He then completed two victories in the Davis Cup against Hungary. He lost to Danai Udomchoke in straight sets in the second round of the SAT Bangkok Open. Four first round exits in Challengers followed. He then reached the quarterfinals after qualifying of two successive Challengers at the Trofeo Paolo Corazzi and Aegon Trophy. He reached the second round of the Aegon Championships after defeating Iván Navarro, but lost in two tiebreaks to Gilles Simon. In Wimbledon where he got a wildcard as the 2008 juniors champion he won the first set of his first-round match against Igor Kunitsyn but then suffered a knee injury. Despite this he attempted to continue but lost the following ten games before he retired.

He was granted a wildcard to the main draw of the Swedish Open but lost in the first round to Guillermo Cañas. He reached the quarterfinals of the Challenger Open Castilla y León losing out in three sets to Marcel Granollers. He then lost in the second round to Martin Fischer in straight sets at the American Express – TED Open. As the 2008 winner of the US Open boys tournament he was granted a wildcard for the US Open qualification tournament. He won his first round match against Tobias Kamke but in the second round lost to the number one seed of the qualification, Thomaz Bellucci. Dimitrov won his first doubles Challenger title at the ATP Challenger Trophy with Teymuraz Gabashvili beating Jan Minář and Lukáš Rosol. He then received a wildcard at the If Stockholm Open but lost in the first round to Jarkko Nieminen.

Dimitrov started the season with a quarterfinal finish at a challenger event of Internationaux de Nouvelle-Calédonie. He then attempted to qualify for the Australian Open, but lost in the first round to Robert Kendrick in three sets.

Grigor Dimitrov in 2010

He bounced back a week later by qualifying at the Honolulu Challenger, but lost to Donald Young in the second round. Dimitrov then participated for Bulgaria in the Davis Cup, claiming all three wins in a 3–2 victory over Monaco. Following the Davis Cup tie, Dimitrov had a number of early losses in various challenger tournaments. Dimitrov won his first ATP tour match of the year on the grass courts of the Aegon Championships in London. He beat Alex Bogdanovic before losing to world No. 31, Feliciano López, in the second round. He then had a great run in the Marburg Open, a Challenger event, where he came through qualifying to reach the semifinals where he lost out to Simone Vagnozzi. Dimitrov again had a number of disappointing losses in Challenger events and another Davis Cup tie. Dimitrov then participated in four futures tournaments, posting impressive results, including two tournament victories in Germany, and another in Spain. Dimitrov gained enough points to enter the world's top 250 for the first time in his career.

His recent good form translated to the Challenger Tour, capturing three consecutive titles, the first coming at the IPP Trophy, defeating Pablo Andújar in three sets. And back to back titles at the Bangkok Open, where he beat former top 20 player Dmitry Tursunov in the quarterfinals and Konstantin Kravchuk in the final, and at the Bangkok Open 2 defeating Alexander Kudryavtsev.[21][22] He made an early exit in his first Challenger after a two-week break but bounced back a week later, beating top 100 player Lukáš Lacko and world No. 32 Michaël Llodra on the way to the final of the Open d'Orléans. In the final, Dimitrov lost to Nicolas Mahut in a third set tiebreak. After two disappointing Challenger tournaments in Germany, in which Dimitrov suffered first round exits, he reached the semifinals of IPP Open, his last tournament of the year. There he played Lithuanian youngster Ričardas Berankis. After the loss of a tight first set in a tiebreak, Dimitrov dominated the second set but was dominated in turn by Berankis in a third set loss. In an off-court incident after the match, Dimitrov pushed the chair umpire with both hands and swore at him because he felt he was treated unfairly after some close calls in the first set tiebreak. Dimitrov was fined €2,000. By reaching the semifinals in Helsinki, Dimitrov reached his best ever ATP world ranking (106).

His first tournament of the year was the Australian Open where he advanced through the qualifying rounds with the loss of just one set. He defeated world No. 38, Andrey Golubev, to advance for the first time to the second round of a Grand Slam tournament where he lost to 19th seed Stanislas Wawrinka. Nonetheless, Dimitrov achieved his top ever ATP ranking ending January at 85. Thus, he became the top ranked Bulgarian male tennis player of all time. Dimitrov then qualified for the ABN AMRO World Tennis Tournament but lost to eighth seed Jo-Wilfried Tsonga in the first round in two sets.[23] He then lost in the first rounds of the Open 13 and Dubai Tennis Championships to Dmitry Tursunov and Richard Gasquet respectively. Dimitrov then won the Challenger DCNS de Cherbourg defeating defending champion and number two seed Nicolas Mahut in the final. He then qualified for the Sony Ericsson Open losing to Sergiy Stakhovsky. Dimitrov became the first Bulgarian man ever to be seeded at an ATP World Tour tournament being seeded eighth at the U.S. Clay Court Championships but lost in the second round to Teymuraz Gabashvili. At the Barcelona Open Banco Sabadell, he lost in the first round to Juan Mónaco. He reached his first quarterfinal in an ATP tournament at the BMW Open after defeating Marcos Baghdatis but lost to Florian Mayer in three sets. Dimitrov lost in the first round of the French Open to Jérémy Chardy.

Dimitrov then advanced to his second ATP quarterfinals at the Aegon International after he defeated sixth seeded Kevin Anderson in the second round, but lost in the third round to third seed Janko Tipsarević. He also competed in the doubles with Andreas Seppi and became the first Bulgarian man ever to reach a doubles final at an ATP tournament, they lost to Jonathan Erlich and Andy Ram. At Wimbledon, he lost a memorable second round match to Jo-Wilfried Tsonga, in a tight four-setter. He then reached the second rounds of the Campbell's Hall of Fame Tennis Championships and Farmers Classic, losing to Americans Denis Kudla and Alex Bogomolov, Jr.. At the Atlanta Tennis Championships, he fell to Rajeev Ram in the first round. At the Western & Southern Open Dimitrov defeated Marsel İlhan in the first round, but lost to world No. 6, David Ferrer, in the second round in three sets.[24] He also reached the third round of the Winston-Salem Open being defeated by Alexandr Dolgopolov in a third set tie-break. At the US Open Dimitrov was defeated by Gaël Monfils in the first round.[25] At the Open de Moselle, Dimitrov was beaten in 53 minutes by qualifier Igor Sijsling in the first round.[26] After that, in the Thailand Open, Dimitrov beat Ivan Dodig and Simone Bolelli, before falling to Andy Murray in the quarterfinals in two sets.

In his next tournament, at the China Open, he lost once again to top-seeded Jo-Wilfried Tsonga in the first round. At Shanghai Rolex Masters Dimitrov beat Marsel İlhan in the first round but was defeated by Andy Roddick in the second round in two tight sets.[27] At the If Stockholm Open Dimitrov beat Ryan Sweeting and Juan Ignacio Chela before losing to Milos Raonic in the quarterfinals.[28] He ended the year ranked No. 76.

Dimitrov started his 2012 season by competing at the Hopman Cup alongside Tsvetana Pironkova. Their team was defeated by the Czech Republic 1–2, after they won a match in mixed doubles but lost their singles matches. Then, their team defeated Denmark 2–1.[29] Against USA, Dimitrov trounced Mardy Fish in straight sets in his first win (although not official ATP win) against a Top 10 player. At the Australian Open Dimitrov defeated Jérémy Chardy to reach the second round but then he lost in five sets to Nicolás Almagro. Dimitrov competed in the SAP Open but lost in the first round to Kevin Anderson, despite winning the first set easily, lost the next two in tie-breaks.[30]

At the BNP Paribas Open Dimitrov defeated Ivan Dodig in the first round, but lost to David Ferrer in the second round. Dimitrov's next tournament was the Sony Ericsson Open, where he reached the fourth round after defeating Mikhail Kukushkin, Juan Ignacio Chela, and upsetting world No. 7, Tomáš Berdych, his first win over a top-ten player, before losing to Janko Tipsarević.[31][32] Dimitrov entered the challenger event Strabag Prague Open as the fifth seeded player. In the first round he defeated Jan Hájek and then lost to Aljaž Bedene in the second. At the French Open, Dimitrov was a set and a break up against 17th seed Gasquet before suffering an injury, he went on to lose the set, momentum and eventually match.

Dimitrov at the 2012 US Open

Dimitrov's next tournament was the Aegon Championships. He beat Bobby Reynolds, Gilles Müller and Nicolas Mahut and then reached his first ATP semifinal by beating the No. 9 seed, Kevin Anderson by coming back from a set down. Dimitrov became the first ever Bulgarian male tennis player to reach an ATP semifinal.[33] In his first ATP semifinal Dimitrov lost to tenth seeded David Nalbandian in straight sets.[34] This tournament helped him become #65 in the rankings.

At the 2012 Wimbledon Championships, Dimitrov faced the No. 32 seed, Kevin Anderson in the first round. Dimitrov won in a very close four sets. In the second round, he faced the Cypriot Marcos Baghdatis, where Dimitrov retired due to an injury. His next tournament was Swedish Open. Seeded sixth, he eliminated Rogério Dutra da Silva, Frederico Gil, and third seed Albert Ramos all in straight sets to reach a second ATP semifinal in his career. In the semifinal, he lost to the top seed and eventual champion David Ferrer in straight sets. Dimitrov then competed in the Crédit Agricole Suisse Open Gstaad. He defeated sixth seed Julien Benneteau, Dustin Brown, and Łukasz Kubot. In his third career semifinal, he lost again – this time to Thomaz Bellucci in two tough tiebreaks. On the grass of Wimbledon, Dimitrov represented his country for the first time in the Olympics. In the first round, he defeated Pole Łukasz Kubot again in two tight sets, two weeks after he had beaten him in the Swiss Open quarterfinal. He fell in the second round to the 12th seed, Gilles Simon – his fourth loss against Simon (whom he has never beaten).

On hard courts, Dimitrov has failed to qualify for Rogers Cup and Western & Southern Open. In both Master tournaments, he lost in the first round of the qualifying round to Marco Chiudinelli and Rajeev Ram respectively. Dimitrov suffered a first lost at the final slam of the year, the US Open to Benoît Paire in four sets. He ended his drought at the PTT Thailand Open, reaching the second round before losing to Richard Gasquet in three tight sets. He then qualified for the Japan Open, but fell to Juan Mónaco in straight sets.

At the Masters event of Shanghai, he defeated Pablo Andújar before losing to world No. 2 Novak Djokovic. At the Swiss Indoors Basel Dimitrov reached the quarterfinals, defeating Viktor Troicki in straight sets and Julien Benneteau in three tie-break sets, before losing to Paul-Henri Mathieu in two tie-break sets. His next tournament was the BNP Paribas Masters, after receiving an entry from the qualifying draw. He beat Jürgen Melzer before his 2012 campaign ended at the hands of Juan Mónaco.[35] Dimitrov ended 2012 ranked world No. 48 in singles.

Dimitrov began his 2013 season by competing at the Brisbane International. He defeated Brian Baker, world No. 13 Milos Raonic, Jürgen Melzer, and Marcos Baghdatis to reach his first ATP singles final, thus becoming the first Bulgarian player to reach an ATP final.[36][37][38] He lost to world No. 3 and defending champion Andy Murray in straight sets, despite being a break up in both sets.[39] Dimitrov paired Kei Nishikori in the doubles and reached the semifinals, but withdrew due to Nishikori's injury. This performance also meant that Dimitrov surpassed $1 million earned in prize money,[40] a feat which no other male Bulgarian tennis player has accomplished. In his next event, the Apia International, Dimitrov suffered a first-round straight-set loss to Italian Fabio Fognini.[41]

At the Australian Open, Dimitrov suffered a first-round straight-set defeat by Julien Benneteau.[42] He also competed in the men's doubles event with Marcos Baghdatis. The pair defeated fourth seeds Max Mirnyi and Horia Tecău in the second round,[43] before losing to Juan Sebastián Cabal and Robert Farah Maksoud in the third round in two close tie-break sets.[44] Despite losing in the first round, Dimitrov became the first male Bulgarian player to rank inside the top 40 after the event.[45] He then competed for Bulgaria in the Davis Cup against Finland, and won both his singles matches against Juho Paukku and Micke Kontinen, but lost his doubles in five sets (with partner Dimitar Kuzmanov) against Henri Kontinen of Finland and Harri Heliövaara. Finland ended up winning the tie 3–2.

At the PBZ Zagreb Indoors, Dimitrov lost in the first round to Ivo Karlović in two tie-breaks.[46] At the ABN AMRO World Tennis Tournament, Dimitrov beat Bernard Tomic and Nikolai Davydenko, and Marcos Baghdatis in three sets.[47][48][49] In the semifinals, Dimitrov lost against world No. 7 and eventual champion Juan Martín del Potro in straight sets.[50] At the BNP Paribas Open, Dimitrov became the first Bulgarian male tennis player to be seeded in a Masters 1000 event.[51] In singles, he beat Matthew Ebden in two sets, but lost to world No. 1 Novak Djokovic in the third round.[52] In doubles he partnered with Frederik Nielsen; they lost to Ivan Dodig and Marcelo Melo in the second round.[53] At the Sony Open Tennis, Dimitrov beat Simone Bolelli, but lost to second seed Andy Murray in straight sets in the following round.[54] In doubles with partner Frederik Nielsen, they reached semi-finals losing in straight sets against the eighth seeds, Mariusz Fyrstenberg and Marcin Matkowski.[55]

Dimitrov at the 2013 Monte-Carlo Masters

Dimitrov's next tournament was the clay-court Monte-Carlo Masters, where he reached the quarterfinals beating Xavier Malisse, eighth seed Janko Tipsarević, and Florian Mayer, all in straight sets, but lost in three sets to eight-time defending champion and third seed Rafael Nadal.[56] This good run in Monte Carlo meant Dimitrov entered the top 30 in the ATP rankings for the first time, at No. 28. His next event was Barcelona Open Banco Sabadell, seeded 14th, he received a bye, but lost in the second round, despite leading 5–2 in the first set, he lost in straight sets to in-form Tommy Robredo.[57]

At the Madrid Open, following a victory over fellow 21-year-old Javier Martí, Dimitrov recorded the biggest win of his career, defeating world No. 1, Novak Djokovic in a three set match, in just over three hours. The two had met twice before, with Djokovic taking both encounters. In the third round, despite winning the first set, he lost in three sets to 15th seed Stan Wawrinka.[58]

Dimitrov's next event was at the Internazionali BNL d'Italia. In what was his fourth victory over the Cypriot out of five matches, he beat Marcos Baghdatis in straight sets in the first round, with one break of serve deciding both sets. In the second round he lost in straight sets against ninth seed and world No. 9 Richard Gasquet – his fourth loss against the Frenchman out of four matches.[59]

At the Roland Garros Dimitrov was seeded 26th, thus becoming the first ever Bulgarian male tennis player to be seeded at a Grand Slam tournament.[60] He beat Alejandro Falla in the first round, after the Colombian retired trailing one set to love and one game down in the second set, citing an elbow problem.[61] Dimitrov eliminated wildcard world No. 324, Lucas Pouille, in straight sets in the second round, thus becoming the first ever Bulgarian male tennis player to reach the third round of a Grand Slam.[62] He lost in straight sets against world No. 1 Novak Djokovic in the third round.[63] Dimitrov also played in the doubles with partner Frederik Nielsen losing in straight sets to seventh seeded Alexander Peya and Bruno Soares in the second round.

Dimitrov at Wimbledon, 2013

In the grass season, Dimitrov played the Aegon Championships, where he was seeded tenth. He faced Dudi Sela in the first round, he came back from a set down and won the third set in a tie-break, but lost to four-time champion Lleyton Hewitt in the second round in straight sets. He then played the Boodles Challenge, an exhibition event, he lost to Janko Tipsarević and Novak Djokovic on a match tie-break, but defeated Jerzy Janowicz in straight sets.[64] At the Wimbledon Championships, Dimitrov eliminated Simone Bolelli in straight sets and then lost in the second round to world No. 55 Grega Žemlja 11–9 in the fifth set.[65]

At Swedish Open Dimitrov reached semifinals for his second consecutive year. He eliminated Elias Ymer and Filippo Volandri in three sets, and upset world No. 20 Juan Mónaco in the quarterfinals, in straight sets.[66] In the semifinals he lost to Fernando Verdasco, in an epic three set battle.[67] He then started his US Open Series campaign at the Citi Open, Dimitrov received a bye and defeated Xavier Malisse and Sam Querrey in straight sets.[68][69] In the quarterfinals, Dimitrov lost in two tiebreak sets to the German veteran Tommy Haas.[70] At the Rogers Cup, he fell in the first round the Spaniard Marcel Granollers in straight sets, but rebounded at the Western & Southern Open, defeating world No. 15 Nicolás Almagro and Brian Baker, before losing to Rafael Nadal in three sets in the third round. The Bulgarian then suffered three consecutive first round exits at the US Open to João Sousa in five sets, the China Open to Roberto Bautista Agut in straight set, and the Shanghai Rolex Masters to Kei Nishikori in straight sets as well.

At the Stockholm Open Dimitrov won his first ATP title by defeating top seed David Ferrer in the final, coming back from a set down, becoming the first ever male Bulgarian player in the Open era to win such a title. This win also meant Dimitrov reached a career-best No. 22 in the world. He followed it up with a quarterfinal showing at the Swiss Indoors defeating Radek Štěpánek and Alexandr Dolgopolov in straight sets, before losing to childhood idol Roger Federer in two tight sets. He played his final event of the year at the BNP Paribas Masters, where he beat Michaël Llodra and Fabio Fognini, both in three sets, but then lost to Juan Martín del Potro in the third round, despite winning the first set. Dimitrov finished the year ranked 23rd in singles and 68th in doubles.

On 16 December 2013, Dimitrov received the second most votes for the Bulgarian Sportsperson of the Year award, earning 1331 points and finishing just behind wrestler Ivo Angelov.[71]

Dimitrov started the 2014 season ranked 23rd. His first event was the Brisbane International, where he took part in the last event too and reached his first final at that time. He was now seeded fifth. However, now he was unable to repeat that good performance, winning in the first round in two sets against Robin Haase in under one hour, but then losing against Marin Čilić in two sets,[72] losing both sets to five games with a break of his serve in the last game deciding both sets. He also competed in the doubles with partner Jérémy Chardy and won in the first round against Brits Fleming and Hutchins[73] (winning the deciding champion tiebreak), but then lost in the second round against Federer and Mahut[74] in a match which featured three tiebreaks, with a champion tiebreak again deciding the match. Dimitrov then played at the exhibition tournament in Kooyong, Australia, an event which featured top players Richard Gasquet, Stan Wawrinka and Tomáš Berdych. However he failed to take a single victory (losing in straight sets to Kei Nishikori[75] and Fernando Verdasco[76]), and ultimately pulled out prior to the seventh place playoff.

Seeded 22nd at the Australian Open, Dimitrov had his best run at a Grand Slam event, defeating Bradley Klahn,[77] Lu Yen-hsun,[78] eleventh seed Milos Raonic and Roberto Bautista Agut in succession, leading him to his first ever major quarterfinal, where he lost to top seed and world No. 1 Rafael Nadal in four sets[79] after winning the first and also having three set points to win the third. As a result of this career-best run at a Grand Slam tournament, Dimitrov entered the world's top 20 for the first time (at No. 19),[80] becoming the first ever Bulgarian male tennis player to do so.

Next, in February, he played at the Rotterdam indoor event, where he was seeded eighth. Dimitrov beat world No. 28 Dmitry Tursunov in the first round 2–1 sets. Dimitrov then lost to world No. 24 Ernests Gulbis in straight sets.[81]

Dimitrov with the trophy at the Acapulco event

Dimitrov played in the Acapulco hard court event, where he was seeded 4th. Dimitrov beat world No. 71 Marinko Matosevic in the first round and Marcos Baghdatis in the second in straight sets. In the quarterfinals Dimitrov beat seventh seed and world No. 18 Ernests Gulbis in two sets to one in a match lasting over 2½ hours. In the semifinals Dimitrov beat second seed and world No. 7, Andy Murray for the first time in a match that lasted almost three hours – losing the first set then overcoming the Brit in two tiebreaks; thus, reaching his third ATP final where he defeated Kevin Anderson in three sets. The victory was Dimitrov's first win at an ATP 500 level tournament[82] and with it he reached his highest ever ATP rank – No. 16. Following his win, Dimitrov played at Indian Wells, an ATP 1000 event, where he was seeded 15th and received a bye into the second round where he beat Robin Haase in straight sets, but then lost in the third round in two sets to one to world No. 22, Ernests Gulbis, who reached the quarterfinal.

Dimitrov then played in Miami, where he was again seeded 15th and had a bye in the first round. He beat Albert Montañés 2–1 sets (losing the second set on a tiebreak) in round two. In the third round, in what was his second loss against the Japanese out of two matches between them, he lost in a tight two sets to 20th seed Kei Nishikori, who went on to reach the semifinals. After Miami, Dimitrov reached a new career-high ranking of No. 15.

Next, in April, he played for the Bulgarian Davis Cup team in the Europe Group II playoffs between Greece and Bulgaria. In the opening match of the tie, he beat No. 690 teenager Markos Kalovelonis 3–0 sets, losing just six games. He then teamed up with No. 344 Dimitar Kutrovsky, who previously brought a 2nd win for Bulgaria, and they beat the Greek team of Alexandros Jakupovic and Markos Kalovelonis 3–0 sets, thus bringing the tie to a crucial 3–0 lead, meaning Bulgaria keeps their Europe Group II position for 2015 and Greece gets relegated to Europe Group III.

Just before Monte Carlo, Dimitrov reached a new career-high ranking of No. 14.[83] At the Monte-Carlo Masters clay-court event, he was seeded 12th. Dimitrov beat in-form No. 32 Marcel Granollers 2–1 sets in the 1st round, then another Spaniard – qualifier Albert Ramos, ranked just outside the top-100, also 2–1 sets. However, in what was his fourth loss out of five matches between them, Dimitrov lost 2–0 sets to sixth seed David Ferrer in round three.

He then played in the Bucharest clay-court event, where he was given a wildcard and was the top seed and had a bye in the first round. In what was the first meeting between the two, in round two Dimitrov beat No. 79 Jiří Veselý 2–0 sets. He beat Sergiy Stakhovsky 2–0 sets in round three, then beat third seed No. 24 Gaël Monfils in the semifinals after leading in the first set when Monfils retired,[84] thus reaching his fourth ATP final. In the final, Dimitrov defeated Lukáš Rosol 2–0 sets, winning the first on a tie-break, then winning the second set with the loss of just one game to win his third ATP title and first one on clay.[85]

In May, he played in the Madrid Open clay-court event, where he was seeded 12th. Dimitrov beat local wildcard Pablo Carreño Busta 2–0 sets in the first round,[86] then in the second round another wildcard – No. 164 Marius Copil – 2–1 sets, coming back from a set down, winning the deciding set on a tie-break. However, in what was his first loss against the Czech out of three matches between them, in round three he lost 2–1 sets to sixth seed No. 6, Tomáš Berdych, after winning the first set.

Dimitrov then played at the Italian Open, where he was again seeded 12th. He beat No. 47 Édouard Roger-Vasselin 2–1 sets, No. 52 Ivo Karlović 2–0 sets, then sixth seed, Tomáš Berdych, 2–1 for a third victory against the Czech out of four matches between them, then 15th seed Tommy Haas in the quarterfinals, after the German retired while losing 1–0 in sets. In what was the fifth match between them and the first match that Dimitrov was unable to win a set in, he lost 2–0 sets to first seed, Rafael Nadal, in the semifinals. This reaching of the Rome semifinal was Dimitrov's best ATP Masters performance. He also successfully played in the Rome doubles with partner Lukáš Rosol and they beat unseeded world No. 4 Colombian pair Juan Sebastián Cabal and Robert Farah Maksoud in the first round 2–0 sets, winning both sets on a tie-break. In the second and third rounds, they beat second seeded Austrian-Brazilian duo of Alexander Peya and Bruno Soares then unseeded Marin Čilić and Santiago González, both 2–1 sets. They lost 2–0 sets to undeeded Robin Haase and Feliciano López in the semifinals. This performance meant Dimitrov reached a new career-best singles ranking of 12th,[87] and also moved 58 places up the doubles rankings, to No. 84.[87]

He then played at Roland Garros, where he was seeded 11th. In round one he lost 3–0 sets to big-serving No. 37 Ivo Karlović, whom he recently beat in Rome.

In June 2014, Dimitrov played at the Queens grass-court event, where he was seeded fourth and had a bye into round two. He beat local No. 168 James Ward in round two, then No. 53 Édouard Roger-Vasselin in the third round, both 2–0 sets. Dimitrov was due to play eighth seed Alexandr Dolgopolov in the quarterfinals, but received a walkover when the Ukrainian retired before the match, citing a thigh injury. Dimitrov then faced first seed, Stan Wawrinka, in the semifinals, and won in straight sets. Dimitrov claimed his first title in a grass court against Feliciano López in three sets, being a set behind and saving a match point. It was the event's first time in which the final was decided with three tiebreakers, as well as being the longest ever Queens final. Dimitrov also played in the Queens doubles event, with partner world No. 3 Wawrinka (ranked outside the top 150 in the ATP doubles rankings), and in round one they beat local brother wildcard duo of Ken and Neal Skupski in straight sets, but then lost in a tight two-setter to third-seeded Canadian-Serbian veteran duo of Daniel Nestor and Nenad Zimonjić in the second round.

Next, Dimitrov played at the 2014 Wimbledon Championships, where he was seeded 11th. In rounds one and twp he beat two qualifiers —No. 150 Ryan Harrison and No. 236 Luke Saville, both in three sets. In round three, in what was his second victory against the Ukrainian out of three matches, he beat 21st seed Alexandr Dolgopolov in a five-set match, coming back from 2–1 sets down. Dimitrov followed that up with a straight sets victory over No. 64 Leonardo Mayer in round four. In the quarterfinals, in what was his second victory against the Brit out of five matches, he beat defending Wimbledon champion and third seed Andy Murray 3–0 sets. This win meant Dimitrov reached his first Grand Slam semifinal, becoming the first male Bulgarian player to reach that stage. He was beaten in four sets by first seed No. 2, Novak Djokovic, who went on to win the tournament. This good performance also meant Dimitrov entered the top-10 ATP rankings for the first time – at No. 9 – becoming the first ever Bulgarian male tennis player to do so.[88]

In the end of July, Dimitrov was due to play at the Washington Open hard-court event, where he was seeded third, but had to withdraw due to flu and sinus problems. In August, he played at the Canadian Open Masters, where he was seeded No. 7 and had a bye into the second round. In the second and third rounds Dimitrov beat Donald Young and 17th seed Tommy Robredo, both 2–1 sets. Then, in the quarterfinals, in what was his fifth victory against the South-African out of six matches between them, he beat No. 21, Kevin Anderson, 2–1 sets, coming back from a set down and winning the deciding set on a tiebreak. In the semifinals, he lost to 13th seed and eventual champion, Jo-Wilfried Tsonga.

Next, Dimitrov played at the Cincinnati Masters. He was seeded seventh again and had a bye into the second round where he lost to Jerzy Janowicz. At the US Open, Dimitrov was seeded seventh. After Dimitrov defeated Ryan Harrison in the first round, Dudi Sela in the second, and David Goffin in the third, he lost to 20th seed Gaël Monfils in the round of 16 in three close sets, which dropped his tennis ranking to No. 10 after the tournament.

Along with Novak Djokovic and Rafael Nadal, Dimitrov competed in the annual September China Open tournament in Beijing. After defeating Fernando Verdasco and Pablo Andújar, Dimitrov lost to world No. 1 Djokovic in the quarterfinals. Dimitrov's next tournament was the Shanghai Rolex Masters, where he was seeded 10th. After defeating Denis Istomin in the first round, Dimitrov lost to the unseeded Julien Benneteau in the second round.

Dimitrov began the defence of his ATP maiden title in Stockholm, winning his second- and third-round matches with Teymuraz Gabashvili and Jack Sock.[89] He beat Bernard Tomic in the semifinals, reaching his sixth career ATP World Tour singles final. Dimitrov lost the final to Tomáš Berdych in three sets.[90]

In Basel, Dimitrov beat teenager Alexander Zverev and Vasek Pospisil in first and second rounds, before losing to top-seeded and eventual champion Roger Federer at the quarterfinals for a second year in a row. At the Paris Masters, Dimitrov beat Pablo Cuevas in the second round, but then lost to Andy Murray in the third. This was his last tournament for the year. Dimitrov had an opportunity to qualify for the 2014 ATP World Tour Finals, but he finished 11th. On 22 December 2014, Dimitrov was chosen as the Bulgarian Sportsperson of the Year (earning 1190 points), becoming the first tennis player to win the award.[91]

Dimitrov started the year ranked No. 11. In the beginning of January, he began his season at the Brisbane outdoor hard-court event, where he was seeded fourth and received a bye into the second round. There Dimitrov beat Jérémy Chardy, coming back from a set down and winning the deciding set on a tiebreak. In the quarterfinals, he beat Martin Kližan in straight sets, but then lost to world No. 2 and eventual champion Roger Federer at the semifinals in less than an hour. Dimitrov also played in the doubles event, paired with the Australian teenager Thanasi Kokkinakis, with whom he reached the semifinals.

At the Australian Open, Dimitrov was seeded tenth. In the first round he overcame Dustin Brown in just 69 minutes, then in the second round he beat Lukáš Lacko in four sets and Marcos Baghdatis in five sets in the third round. Dimitrov lost to sixth seed and eventual runner-up, Andy Murray, in the fourth round in four sets. In February, Dimitrov participated in the Rotterdam Open indoor hard-court event, where he was seeded fifth. In the first round he beat the qualifier Paul-Henri Mathieu 2–1 sets, saving two match points in the second set, but then lost in straight sets to world No. 37, Gilles Müller, in the second round. Dimitrov played in Acapulco next, where he was the defending champion and seeded third. He lost in the second round to Ryan Harrison. On 10 March 2015, Dimitrov played at an annual exhibition tournament in Madison Square Garden against Federer, defeating the Swiss star for the first time.[92]

In March Dimitrov played at the Indian Wells Masters, where he was seeded 11th and had a bye into the second round, where he beat in three sets the Australian teenager and world No. 37, Nick Kyrgios. Dimitrov lost to world No. 19, Tommy Robredo, in the third round. Dimitrov also played at the doubles event, paired with Mardy Fish, but they lost in the first round to Spaniards David Ferrer and Fernando Verdasco. Dimitrov was seeded ninth at the Miami Masters and had a bye into the second round, where he beat Vasek Pospisil, but then lost to the 22nd seed John Isner in the third round. Dimitrov began his clay season at the Monte-Carlo Masters. He was seeded ninth and beat Verdasco in the first round, and then defeated in straight sets Fabio Fognini in the second round. In the third round, Dimitrov crushed in less than an hour the seventh seed and defending champion Stan Wawrinka and then lost in straight sets to Gaël Monfils in the quarterfinals. Dimitrov also played in the doubles, paired with Max Mirnyi. They reached the second round, where they lost to the Bryan brothers.

Dimitrov decided not to defend his title in Bucharest, and instead he participated in the first edition of the Istanbul event. He was seeded second and had a bye into the second round, where he defeated Andrey Golubev. In the quarterfinals Dimitrov beat Ivan Dodig, but then lost to Pablo Cuevas in the semifinals. Next, Dimitrov played at the Madrid Masters, where he was seeded tenth. His opponent in the first round Donald Young retired, after Dimitrov was leading by a set and by 3–0 games in the second set. Then, Dimitrov beat Fabio Fognini, coming back from a set down, and overcame eighth seed Stan Wawrinka in three sets in the third round. At the quarterfinals, Dimitrov lost in straight sets to third seed and two-time defending champion Rafael Nadal, which was his sixth defeat out of six matches between them. Dimitrov also played in the doubles and reached the second round.

Dimitrov was unable to defend his semifinal at the Rome Masters in May. He was seeded 10th and beat in straight sets Jerzy Janowicz in the first round, but then lost in three sets to Fabio Fognini, in what was the third match between them within a month. Next, Dimitrov lost in straight sets to Jack Sock at the French Open in the first round despite being seeded tenth. Dimitrov exited the tournament early for a second year in a row.

In June, Dimitrov failed to defend his title at the Queens grass-court event, losing in the second round to Gilles Müller. Next, being seeded 11th, he played at the Wimbledon Championships and in the first two-round eliminated Federico Delbonis and Steve Johnson. Dimitrov lost in straight sets to Richard Gasquet in the third round, in what was his fifth defeat out of five matches against the Frenchman. Following that defeat, Dimitrov decided to part ways with coach Roger Rasheed.[93]

In July, he participated in the 2015 Davis Cup against Luxembourg, winning all his matches. In August, he started his US Open series campaign in Washington, reaching the third round. Then, he played at the Rogers Cup, losing to Jack Sock in the second round. At the Cincinnati Masters, Dimitrov was eliminated in the third round by the world No. 2, Andy Murray, having missed a match point in the third set. Dimitrov's weak performance continued at the US Open, where he lost in five sets to Mikhail Kukushkin in the second round.

In September he hired Franco Davín as his coach.[94] Dimitrov reached the quarterfinals in Kuala Lumpur and then in the beginning of October had another first round exit in Tokyo. After these tournament Dimitrov dropped out of top 20. After an unsuccessful Asia swing, Dimitrov traveled to Sweden to participate in the Stockholm Open and reached the quarterfinals where he was defeated by Tomáš Berdych in straight sets. Following that tournament, he traveled to Basel for the Swiss Indoors where he lost to Rafael Nadal in three sets in the round of 16. His last tournament for the year was Paris, where Dimitrov managed to eliminate Marin Čilić, before losing to Ferrer. He did not qualify for the ATP World Tour Finals.

Ranked world No. 28, Dimitrov began the season in Brisbane, where he reached the quarterfinals, losing to Federer. Paired with Kei Nishikori, Dimitrov also reached the semifinals in the doubles, but withdrew due to shoulder soreness. The Bulgarian reached his seventh career final in Sydney, losing to the defending champion Viktor Troicki in three sets and a tie-break in the third set. Next, Dimitrov recorded another defeat to Federer, his fifth overall between the two, in the third round of the Australian Open.

In February, Dimitrov decided to skip the first edition of Sofia Open in his homeland and participated in the Delray Beach event, where he lost to the unseeded Rajeev Ram in the semifinals. Next, Dimitrov lost to the in-form and eventual champion Dominic Thiem at the quarterfinals in Acapulco.

In March, seeded 23rd, Dimitrov had a bye into the second round of the Indian Wells Masters, but was upset by the German teenager Alexander Zverev. Dimitrov also had a bye into the second round of the Miami Open. In the third round, he overcame the world No. 2, Andy Murray, coming back from a set down, but then lost to Gaël Monfils.

In April, Dimitrov began his clay-court season. He reached the second round of the Monte-Carlo Masters, losing to the 15th seed Gilles Simon in straight sets. Seeded 2nd, Dimitrov reached his eighth career final in the Istanbul event, beating third seed, Ivo Karlović at the semifinals in two tie-breaks. In the final, against the unseeded Diego Schwartzman, Dimitrov was serving for the match in the second set, but started cramping and then had a complete meltdown. After smashing two rackets, and being warned and penalized, Dimitrov smashed a third racket in the third set, which resulted in a match-ending penalty.[95][96]

At the Madrid Masters in the beginning of May, Dimitrov was unable to defend his quarterfinal from the previous year, suffering a first round exit in straight sets to Pablo Carreño, not having lost even a set to the Spaniard prior to that match. In the following week, Dimitrov's position in the ATP ranking deteriorated further to No.35, a three-year low. The Bulgarian was then beaten again by Alexander Zverev in first round of the Rome Masters. This was followed by another first round loss at Roland Garros to Viktor Troicki, this time in five sets.

In June, Dimitrov's downfall continued, as he played on grass courts in Stuttgart and in London, losing once again in the first rounds to the wildcard Juan Martín del Potro in straight sets, and to the returning from injury Janko Tipsarević, respectively. Being unseeded at a Major for the first time since 2013, Dimitrov ended his losing streak at the 2016 Wimbledon, first beating qualifier Bjorn Fratangelo and then 16th seed Gilles Simon, before losing to Steve Johnson. Soon after that, Dimitrov revealed that prior to Wimbledon he had split with his coach Franco Davín.[97] The Bulgarian hired Daniel Vallverdu as coach.[98]

In July, Dimitrov was seeded 12th in Washington Open and had a bye into the second round, but had another disappointment, as he lost in straight sets to No. 82, Daniel Evans. At Rogers Cup, Dimitrov survived another early elimination against Yūichi Sugita in the first round, coming back from a set down and facing 2–5 in the second set tiebreak. That was followed by an easy win against wildcard Denis Shapovalov and then Dimitrov beat Ivo Karlović in straight sets in the third round. The Bulgarian lost in three sets to third seed Nishikori in the quarterfinals. Paired with Wawrinka, he beat Lucas Pouille and Dominic Thiem in the doubles, before losing to Henri Kontinen and John Peers.

Dimitrov participated in the 2016 Summer Olympics in the first half of August, but lost in the first round to ninth seed Marin Čilić. The Bulgarian then had a good run in Cincinnati, reaching his third career Masters semifinal. He subsequently beat in straight sets Gilles Simon in the first round and then came back from a set to down to eliminate 16th seed, Feliciano López. In the third round Dimitrov won against second seed Wawrinka and then beat Steve Johnson in the quarterfinals, both in straight sets. In the semifinal he was stopped again by the eventual champion Marin Čilić, after allowing re-breaks twice in the third set. With his performance, the Bulgarian secured the second spot in the 2016 US Open Series standings. In the following week, Dimitrov returned in top 30 of ATP ranking, jumping ten positions to No. 24 spot.

Seeded 22nd, Dimitrov played in the 2016 US Open and reached the fourth round for a second time in his career after beating en route Íñigo Cervantes, Jérémy Chardy and João Sousa before losing in straight sets to second seed, Andy Murray, who allowed Dimitrov only five games in total.

Dimitrov moved to Asia to play in the inaugural Chengdu Open. He was seeded third and reached the semifinals, where he lost to fifth seed Albert Ramos-Viñolas. The Bulgarian then went to the final of the Beijing event, beating Steve Johnson, sixth seed Lucas Pouille and gaining first victory over Rafael Nadal, who was ranked No. 4 at the moment. At the semifinals, the third seed, Milos Raonic, withdrew prior to the match with Dimitrov due to ankle injury. Dimitrov lost the final to No. 2, Andy Murray, in two tight sets. The Bulgarian then participated in the Shanghai Masters, where in the first round he overcame in straight sets 14th seed, Richard Gasquet, to whom Dimitrov had had a negative record of 0-5 losses, but in the second lost to qualifier Vasek Pospisil, who had never beaten Dimitrov.

The Bulgarian returned to Europe and reached the semifinals in Stockholm, where he was stopped by the eventual champion Juan Martín del Potro. Dimitrov then played in Basel, but exited the event with a first round loss against Gilles Müller. In his last tournament for the season, the Paris Masters, Dimitrov lost in three sets to No. 1, Novak Djokovic in the third round.

Ranked world No. 17, Dimitrov had a flying start to the season in Brisbane, reaching the final by defeating world No. 8, Dominic Thiem in the quarterfinals and then No. 3 and defending champion Milos Raonic in the semifinals. In the final he overcame world No. 5, Kei Nishikori, in three sets, winning his first ATP title in nearly three years, his last having been at Queen's Club in 2014. Dimitrov next moved on to play in the 2017 Australian Open, where he extended his winning streak further, reaching the semifinals. Dimitrov beat 18th seed, Richard Gasquet, in the third round and 11th seed David Goffin in the quarterfinals, before being eliminated by Rafael Nadal in a five-set thriller, which lasted almost five hours, with Dimitrov failing to convert double break points in the fifth set when the score was 4–3 for Dimitrov.[99] The match with Nadal was later cited among the top 3 of best Grand Slam matches in 2017.[100][101]

In February, Dimitrov competed in the Sofia Open, where he was seeded third. The Bulgarian maintained his excellent start to the season, winning his second title of the year on home soil, defeating second seed, David Goffin, in straight sets in the final.[102] However, the Belgian managed to grab his first victory over Dimitrov, eliminating him in three sets in the quarterfinals of the Rotterdam Open.

In March, Dimitrov played in the Indian Wells Masters, losing in three sets to Jack Sock in the third round, after missing four match points.[103] The Bulgarian then participated in the Miami Open, but was upset by unseeded Guido Pella in the second round.

Dimitrov began his clay-court season with a loss to Tommy Robredo in the second round of the Grand Prix Hassan II tournament, for which he received a wild card and was the top seed. This was followed by another upset at the Monte-Carlo Masters, where Dimitrov was seeded eighth and had a bye into the second round, but lost to qualifier Jan-Lennard Struff.

The Bulgarian ended his losing streak in the Madrid Masters, reaching the third round, where he was eliminated by Dominic Thiem in three tight sets after missing five match points in the third-set tiebreak.[104] Next, Dimitrov had a first-round exit in the Rome Masters, being defeated by Juan Martín del Potro in three sets. This was the fifth loss to the Argentine in five meetings. Dimitrov then went to the third round of Roland Garros, where he lost to Pablo Carreño Busta.

Dimitrov started on grass court in Stuttgart. He was seeded second, but lost in his first match. The Bulgarian then had a good run at the Queen's Club event, where he reached the semifinals. Dimitrov lost in three sets to in-form eventual champion Feliciano López. Without dropping a set, the Bulgarian reached the fourth round at Wimbledon, but then lost in straight sets to eventual champion Roger Federer in what was his sixth defeat in six official matches with the Swiss. Dimitrov returned to the top ten for the first time since February 2015 at the conclusion of the tournament.[105]

Grigor Dimitrov at the 2017 Washington Open

Dimitrov returned to hard courts in August. After reaching third rounds at the Washington Open and the Rogers Cup in Montreal, the Bulgarian won his first Masters 1000 title in Cincinnati, defeating Nick Kyrgios in the final in straight sets, winning the tournament without losing a set. Dimitrov then reached the second round of the US Open, where he lost to teenager Andrey Rublev.

In the beginning of October, Dimitrov reached the semi-finals in Beijing after wins over Juan Martín del Potro and Roberto Bautista Agut, and then the quarterfinals of the Shanghai Masters. In both events the Bulgarian was eliminated by world No. 1, Rafael Nadal, in three-setters.[106] Dimitrov then advanced to the final of the Stockholm Open with wins over Jerzy Janowicz, Mischa Zverev and Fabio Fognini but lost to US Open semifinalist del Potro in straight sets. This was Dimitrov's third final in Stockholm. In the following week, Dimitrov was confirmed to participate for the first time at the ATP Finals, thus becoming the first Bulgarian to qualify for the season-ending championships.[3]

Afterwards, he decided to skip the Vienna Open (despite being given a wild card) due to fatigue, and to prepare for the Paris Masters the following week, where Dimitrov grabbed third victory in a row over Richard Gasquet before losing in the third round to big serving John Isner in three sets. On the following week, prior to the ATP Finals, Dimitrov achieved a new career high, climbing to world No. 6 position.

Dimitrov was drawn in the Pete Sampras group of the 2017 ATP Finals, together with Rafael Nadal, Dominic Thiem and David Goffin. Playing with Thiem in his debut match, Dimitrov clinched a maiden victory in the ATP Finals in a tight three-setter.[107] The Bulgarian then routed Goffin, allowing only two games to his opponent. With this win Dimitrov won the first place in the group and secured his place at the semi-finals.[108] Dimitrov stayed perfect in the group after another convincing victory, this time against alternate Pablo Carreño Busta.[109] The Bulgarian came back from a set down to ultimately eliminate in-form Jack Sock in the semi-finals.[110] Dimitrov won the biggest title of his career by defeating once again David Goffin in three tight sets in the final. He finished the tournament as an undefeated champion, receiving a prize of $2,549,000 and 1,500 ranking points, the latter helped him finish 2017 at a career-high world No. 3 (only behind Nadal and Federer).[111]

Dimitrov ended his 2017 season with these significant milestones [current figure in brackets]: (1) first Masters 1000 title (2) first ATP Finals crown, (3) 5 Tour finals, (4) four tour titles, (5) eight top-10 match wins [had 13 total prior to 2017], (6) 250 career match wins [257 match wins], (7) cracked $10,000,000 in career earnings [$13,103,976], (8) cracked $5,000,000 in a single season [$5,628,512], (9) second Grand Slam semifinal, (10) first Grand Slam semifinal on hard courts.

Dimitrov started his 2018 campaign in Brisbane, where he was the defending champion and top seed. He started from the second round with hard three set win against the home favourite and wild card John Millman, then overcame with another three setter the British number two Kyle Edmund. Dimitrov was eliminated in the semi-finals by the third seed and eventual champion Nick Kyrgios. The Bulgarian played in the doubles as well. Paired with Ryan Harrison, he reached the semi-finals, before withdrawing. Having started his campaign at Australian Open with a couple of wins against qualifiers Dennis Novak and Mackenzie McDonald, Dimitrov was drawn against Andrey Rublev who had knocked him out in the second round of US Open several months before and took revenge, eliminating the 30th seeded Russian. Dimitrov then edged in-form Nick Kyrgios in tight four sets to qualify for his third Australian Open quarter-final, where he lost to Kyle Edmund in four sets.[112] In the following week Dimitrov stated that he had played the last matches with a shoulder injury. Failing to recover, the Bulgarian withdrew from the Sofia Open, where he was defending champion.

In February, Dimitrov reached the final of the Rotterdam Open without dropping a set, defeating Yūichi Sugita, Filip Krajinovic, Andrey Rublev, and David Goffin en route, but eventually lost to Roger Federer, who would regain world No. 1 ranking after the tournament.[113] Next, Dimitrov played in Dubai, where he was top seed, but was upset in the first round by Malek Jaziri.

In March, Dimitrov was third seed at both the Indian Wells and Miami Masters, but faced early eliminations by Fernando Verdasco in the second round and by Jérémy Chardy in the third round, respectively.

Dimitrov rebounded on the next tournament, the Monte-Carlo Masters, advancing to the semi-finals of the clay event after beating No. 10 David Goffin in the quarter-finals. Dimitrov ultimately lost to world No. 1 Rafael Nadal.[114] That was followed by a quarter-final in Barcelona, where Dimitrov lost to Pablo Carreño Busta. After the match ending handshake, Dimitrov accused Carreño Busta of stopping the point in the second set tie-break, which led to an unforced error by the Bulgarian. Carreño Busta denied the accusations.[115]

In May, Dimitrov lost in the second rounds of the Madrid and Rome Masters to Milos Raonic and Kei Nishikori, respectively. Dimitrov then lost in straight sets to Fernando Verdasco in the third round of Roland Garros.

Dimitrov had his worst grass-court season since 2010, having recorded early losses to Novak Djokovic at the Queen's Club tournament and to Stan Wawrinka at the Wimbledon Championships. The second of the defeats came in the first round of the Grand Slam event.

Dimitrov next played in August at the Toronto Masters, where he reached the quarterfinals, losing to Kevin Anderson. Dimitrov then failed to defend his Masters title in Cincinnati after he was beaten in the third round by the eventual champion Novak Djokovic in a tight three-setter. As a result, Dimitrov's ranking dropped to world No. 8. That was followed by first round elimination at the 2018 US Open, with Dimitrov losing to Stan Wawrinka in straights.

Dimitrov contributed to Team Europe for winning the second edition of the Laver cup. However his struggles with form continued after early exits at the China Open and in Vienna, losing to unseeded Dušan Lajović and Mikhail Kukushkin, respectively. Dimitrov's season ended after the Paris Masters, where he lost to fifth seed, Marin Cilic in the third round. Dimitrov didn't qualify for the ATP Finals, where he was the defending champion. Former world No. 1, Andre Agassi, joined Dimitrov's team prior to the Paris Masters.[116]

Dimitrov started his campaign in Brisbane where he defeated Yoshihito Nishioka and John Millman in straight sets before losing to eventual champion Kei Nishikori in the quarterfinals.[117] In January, Dimitrov reached the last 16 of the Australian Open, but was knocked out by Frances Tiafoe in four sets.

Having suffered from a shoulder injury, Dimitrov returned to play in the Miami Masters, reaching the third round. Dimitrov then started his clay court campaign at the Monte-Carlo Masters, where he lost to Rafael Nadal in the third round. Dimitrov then went to the third round of Barcelona Open. His ranking deteriorated to No. 49, the lowest since 2012. At the French Open, Dimitrov upset Marin Čilić in the second round but was subsequently eliminated by Stan Wawrinka in straight sets.[118] Dimitrov had a disappointing Wimbledon, losing to Corentin Moutet in five sets in the first round, despite being up two sets.

Dimitrov's hard court season started off poorly. He lost in the first round of the Atlanta Open to world No. 405 Kevin King, who had never won a main-draw match on the ATP Tour.[119][120] Dimitrov then lost to Stan Wawrinka in the first rounds of both the Rogers Cup and the Western & Southern Open. Following this, Dimitrov had lost seven of his past eight matches, and his ranking had slipped to No. 78, his lowest ranking in over seven years.

At the US Open, Dimitrov was unseeded. He defeated Andreas Seppi in the first round before receiving a walkover over 12th seed Borna Ćorić. He then defeated lucky loser Kamil Majchrzak and Alex de Minaur in straight sets to reach the quarterfinals. There, he faced third seed Roger Federer. In a lengthy five-set match, Dimitrov upset Federer to reach his first Grand Slam semifinal since the 2017 Australian Open. This was also his first career win against Federer, having been defeated on seven previous occasions. He then lost to Daniil Medvedev in the semifinals. As a result of this run, Dimitrov rose 53 ranking places in a single tournament, appearing at No. 25 the next week.

Dimitrov failed to proceed beyond the second round at Chengdu, Beijing, Stockholm, and Vienna. At the Paris Masters, he defeated Ugo Humbert and 12th seed David Goffin to reach the third round, where he defeated the fifth seed Dominic Thiem. In the quarterfinals, he defeated Cristian Garín, before losing to Djokovic in straight sets in the semifinals.

Dimitrov made his Davis Cup debut for Bulgaria in 2008 as a 16-year-old. Playing in front of a home crowd in Plovdiv, the teenage Dimitrov compiled an undefeated record in both singles and doubles to promote his country into the second division of the Europe/Africa zone. A 17-year-old Dimitrov returned to the Bulgarian Davis Cup team for the first round of the Davis Cup Europe/Africa zone in 2009. Dimitrov was victorious in both his singles rubbers which led to a narrow 3–2 victory over Hungary. He would then take a few breaks from Davis Cup which would result in Bulgaria being relegated back to the lowest division of Davis Cup.

Dimitrov would return to Davis Cup competition in 2012 as a top 100 player. The Bulgarians breezed through the round robin tournament held in their home city of Sofia and would once again be promoted to the second division of the Europe/Africa zone. Dimitrov and the Bulgarian Davis Cup team have been unable to advance past the first round since being promoted but have been victorious in their two relegation ties.

Dimitrov represented Bulgaria at his maiden Olympics in London 2012. He competed in the singles competition and advanced past the first round with a straight sets victory over Poland's Łukasz Kubot. He was then beaten by France's 12th seed Gilles Simon. Dimitrov made his second Olympic appearance in 2016 Rio where he was beaten in the first round of the singles competition by Croatian Marin Čilić.

Current through the 2020 French Open.