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.

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.

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[81] and Fernando Verdasco[82]), and ultimately pulled out prior to the seventh place playoff.

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.

[96] 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.

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.

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.

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.

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 wildcard and was the top seed.

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.

In the beginning of October, Dimitrov reached the semifinals in Beijing after wins over Juan Martín del Potro and Roberto Bautista Agut, and then the quarterfinals of the Shanghai Masters.

[113] Afterwards, he decided to skip the Vienna Open (despite being given a wildcard) 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.

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.

In February, Dimitrov reached the final of the Rotterdam Open without dropping a set, defeating Yūichi Sugita, Filip Krajinović, Andrey Rublev, and David Goffin en route, but eventually lost to Roger Federer, who would regain world No.

[123] 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.

[129] He pulled a victory in doubles where as the underdogs he and teammate Alexandar Lazarov stunned the top British experienced pair of Jamie Murray/Joe Salisbury in a close three sets match.

[130][131] In October, Dimitrov reached the fourth round of the French Open for the first time, defeating Roberto Carballés Baena, where he lost to Stefanos Tsitsipas in straight sets.

[140] He then won in the second round defeating ATP Tour debutant and lucky loser August Holmgren (tennis), after Félix Auger-Aliassime withdrawal, in straight sets 6–1, 6–1 in a 56 minutes match to reach his fifth quarterfinal of the season.

[177] Dimitrov reached the fourth round at Roland Garros for the second time at this major, defeating qualifier Timofey Skatov, Emil Ruusuvuori and Daniel Altmaier without losing a set.

In the beginning of the North American Summer swing, seeded fifth, he reached the semifinals at the Washington Open[181] after a walkover from Ugo Humbert, before losing to eventual champion Dan Evans.

[186] He recorded his 400th career win at the 2023 Chengdu Open defeating Juan Pablo Varillas becoming the first man born in the 1990 or later to hit that milestone and the tenth active men's player.

Starting the season at Brisbane,[205][206] he reached his third final at the tournament and 18th in his career overall defeating Andy Murray, Daniel Altmaier, wildcard Rinky Hijikata and Jordan Thompson.

[229] At the 2024 Monte-Carlo Masters, he played the longest best-of-three match in the tournament history lasting 3 and half hours before succumbing to seventh seed Holger Rune in the round of 16.

[235] At the US Open, he reached again the round of 16 for a third Grand Slam in a row in the season, with straight sets wins over qualifier Kyrian Jacquet, Rinky Hijikata and Tallon Griekspoor, not facing a break point in the last match.

Dimitrov skipped the 2020 Tokyo Olympics and registered to play at the ATP 250 tournament in Atlanta instead but later withdrew, as he did not meet the minimal qualifications requirements due to non-representation in the Davis Cup.

He also occasionally dives to reach balls, one of the most famous occasions being his second round match at the Monte-Carlo Masters against Janko Tipsarević, in which he dove to hit a drop-shot, winning him the point.

Dimitrov is also noted as one of the only players on the tour who can consistently produce trick shots, alongside Gaël Monfils, Dustin Brown, Nick Kyrgios and Roger Federer.

Early in his career, Dimitrov was compared to Roger Federer due to their similarity in play style and actions, notably his forehand, backhand and serve, earning him the nickname "Baby Fed".

[275] Historically he has acted as a brand ambassador to Rolex,[276] Haagen Dazs,[276] American Express,[277] Jet Smarter,[278] Vitamin Well,[279] Creed[280] and Telenor[281] and in 2023 entered into multilevel partnership agreement with Bianchet.