Full History Of Grigor Dimitrov In Timeline From 1958

1958: Creation of Bulgarian Sportsperson of the Year Award

In 1958, the Bulgarian Sportsperson of the Year award was created, a distinction Grigor Dimitrov would later win in 2014 and 2017.

1974: Record for comebacks at Wimbledon

In 2024, at the Wimbledon Championships, Grigor Dimitrov was part of the ninth overall comeback from two sets down in a single edition of the All England Club, tying the record (with 1974, 1990 and 1997) for most comebacks at the tournament in the Open Era.

1990: First 1990's man with 400 career wins

In 2023 Grigor Dimitrov recorded his 400th career win making him the first man born in the 1990s to hit that milestone.

1990: Record for comebacks at Wimbledon

In 2024, at the Wimbledon Championships, Grigor Dimitrov was part of the ninth overall comeback from two sets down in a single edition of the All England Club, tying the record (with 1974, 1990 and 1997) for most comebacks at the tournament in the Open Era.

1990: 40 Top 10 Wins for 1990's born

In March 2024 it was noted that Dimitrov became just the third man born in 1990 or later to record 40 or more Top 10 wins after Alexander Zverev and Daniil Medvedev and the eight active player overall.

May 1991: Grigor Dimitrov's Birth

In May 1991, Grigor Dimitrov was born in Bulgaria, marking the beginning of his life and eventual tennis career.

1991: Grigor Dimitrov's birth

In 1991, Grigor Dimitrov was born in Haskovo to Dimitar Dimitrov, a tennis coach, and Maria Dimitrova, a sports teacher and former volleyball player. He began playing tennis at age five and had a strong family influence in sports.

1997: Record for comebacks at Wimbledon

In 2024, at the Wimbledon Championships, Grigor Dimitrov was part of the ninth overall comeback from two sets down in a single edition of the All England Club, tying the record (with 1974, 1990 and 1997) for most comebacks at the tournament in the Open Era.

2005: Best Young Tennis Player in Bulgaria

In 2005, Grigor Dimitrov was awarded as the Best Young Tennis Player in Bulgaria.

2006: Orange Bowl U16 Boys Singles Win

In 2006, Grigor Dimitrov won the Orange Bowl U16 boys singles, marking a significant achievement in his junior career.

2007: Joins Sanchez-Casal Academy

In 2007, Grigor Dimitrov joined the Sanchez-Casal academy to further his tennis training under Emilio Sánchez and Pato Álvarez.

2007: Orange Bowl U18 Finalist and US Open Doubles Final

In 2007, Grigor Dimitrov was a finalist at the Orange Bowl U18 boys singles losing to Ričardas Berankis. He also reached the US Open doubles final with Vasek Pospisil, where they lost to Jonathan Eysseric and Jérôme Inzerillo.

2007: Named Eddie Herr International Rising Star

In 2007, Grigor Dimitrov was named the Eddie Herr International Rising Star, recognizing his potential and achievements in junior tennis.

September 2008: US Open Victory and Junior World No. 1 Ranking

On September 7, 2008, Grigor Dimitrov won the US Open, defeating Devin Britton in the final. This win, along with other victories, led him to become junior world No. 1 on September 8, 2008. Following his US Open victory, Dimitrov announced his decision to end his junior career to focus on his ATP ranking.

2008: Wimbledon Grand Slam Debut and Knee Injury

In 2008, Grigor Dimitrov made his Grand Slam debut at Wimbledon as the junior champion, winning the first set against Igor Kunitsyn. However, he suffered a knee injury and had to retire from the match after losing ten consecutive games.

2008: Various Tournament Performances

In 2008, Grigor Dimitrov participated in the Swedish Open, Challenger Open Castilla y León, Istanbul Challenger, and the US Open qualification tournament, experiencing a mix of successes and losses. He also won his first doubles Challenger title at the ATP Challenger Trophy with Teymuraz Gabashvili.

2008: Junior Grand Slam Performances

In 2008, Grigor Dimitrov reached the quarterfinals of the French Open, won Wimbledon, and won the US Open in the junior circuit, marking a successful year in junior Grand Slam tournaments.

2008: First Men's Title and ATP Level Match

In 2008, Grigor Dimitrov won his first title at a futures tournament in Barcelona on clay. He also participated in his first ATP level match at the Rosmalen Open, where he lost to Igor Andreev. Later, after his junior US Open title, he won back to back futures tournaments in Madrid.

2008: Davis Cup Debut for Bulgaria

In 2008, at the age of 16, Grigor Dimitrov debuted for Bulgaria in the Davis Cup. He achieved an undefeated record in both singles and doubles, contributing to his country's promotion into the second division of the Europe/Africa zone.

March 2009: Joins Mouratoglou's Tennis Academy

In March 2009, Grigor Dimitrov moved to Paris, France, to train at Patrick Mouratoglou's tennis academy for the next four seasons, enhancing his development as a professional player.

2009: Coached by Peter Lundgren

Around the time of his success at the 2009 Rotterdam Open, Grigor Dimitrov began a formal coaching relationship with Peter Lundgren, who previously coached Marat Safin and Roger Federer.

2009: Guaranteed Wimbledon Entry

Grigor Dimitrov's win at Wimbledon in 2008 guaranteed him a wildcard entry into the 2009 Wimbledon men's draw.

2009: Davis Cup Victory Over Hungary

In 2009, 17-year-old Grigor Dimitrov returned to the Bulgarian Davis Cup team and won both of his singles matches, leading to a 3–2 victory over Hungary.

2009: First ATP Tour Main-Draw Win

In 2009, Grigor Dimitrov received a wildcard to the main draw of the Rotterdam Open and scored an upset victory over then-world No. 23, Tomáš Berdych, marking his first ATP Tour main-draw win. In the second round, he faced Rafael Nadal but lost in three sets.

June 2010: Ended Coaching Relationship with Lundgren

In June 2010, Grigor Dimitrov ended his coaching relationship with Peter Lundgren and started to be coached by Peter McNamara.

2010: Sponsored by Nike

From the start of his adult career in 2010, Grigor Dimitrov was sponsored by Nike, wearing the brand's apparel and the Nike Air Zoom Vapor Pro shoes.

NikeCourt Air Zoom Vapor Pro 2 Men's Hard Court Tennis Shoes (DR6191-105, White/Black/Poison Green) Size 11

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2010: Worst Grass-Court Season Since 2010

In 2010, Grigor Dimitrov had his worst grass-court season since then, recording early losses at the Queen's Club and Wimbledon.

2011: Ended Coaching Relationship with McNamara

At the end of the 2011 season, Grigor Dimitrov and Peter McNamara ended their coaching relationship.

November 2012: Joined Good to Great Tennis Academy

On November 26, 2012, Grigor Dimitrov left the Patrick Mouratoglou Academy and joined the Good to Great Tennis Academy in Sweden, run by Magnus Norman, Nicklas Kulti, and Mikael Tillström.

2012: Patrick Mouratoglou Appointed as Coach

In 2012, Grigor Dimitrov appointed Patrick Mouratoglou as his coach, marking a pivotal moment in his professional training and career development.

2012: Behind the Back Drop-Shot

In 2012, Grigor Dimitrov hit a behind-the-back drop-shot against Viktor Troicki in the Swiss Indoors, which was considered the shot of the year.

2012: Olympic Debut in London

In 2012, Grigor Dimitrov represented Bulgaria at the London Olympics, marking his maiden Olympic appearance. He won his first-round match against Łukasz Kubot before being defeated by Gilles Simon.

2012: Return to Davis Cup Competition

In 2012, Grigor Dimitrov returned to Davis Cup competition and helped Bulgaria get promoted to the second division of the Europe/Africa zone after breezing through the round-robin tournament held in Sofia.

2012: Hopman Cup and Win Against Mardy Fish

In 2012, Grigor Dimitrov started his season at the Hopman Cup, partnering with Tsvetana Pironkova. Against the USA team, Dimitrov beat Mardy Fish in straight sets. Although this was not an official ATP win, it was his first victory against a top 10 player.

2012: Wimbledon and Swedish Open Performances

In 2012, Grigor Dimitrov won his first-round match at Wimbledon against Kevin Anderson but retired in the second round due to an injury. He then reached the Swedish Open semifinal but lost to David Ferrer. Additionally, he competed in the Suisse Open Gstaad, reaching another semifinal but lost to Thomaz Bellucci.

2012: Lowest Ranking Since 2012

In 2012, Grigor Dimitrov's ranking deteriorated to No. 49, the lowest since then.

2012: Shanghai Masters and Swiss Indoors Basel Performances

In 2012, at the Shanghai Masters, Grigor Dimitrov defeated Pablo Andújar before losing to Novak Djokovic. At the Swiss Indoors Basel, he reached the quarterfinals before losing to Paul-Henri Mathieu. His 2012 campaign ended after competing in the Paris Masters. Dimitrov ended 2012 ranked world No. 48 in singles.

2012: Begins Dating Maria Sharapova

In late 2012, Grigor Dimitrov began a relationship with Maria Sharapova, a fellow tennis player, marking the start of their public romance.

October 2013: First ATP Tour Singles Title

In October 2013, at the Stockholm Open, Grigor Dimitrov became the first Bulgarian man to win an ATP Tour singles title, marking a significant milestone in his professional career.

October 2013: Hired Roger Rasheed as Coach

On October 7, 2013, Grigor Dimitrov announced that he had hired Roger Rasheed as his new coach.

December 2013: Bulgarian Sportsperson of the Year Award Runner-Up

On 16 December 2013, Grigor Dimitrov received the second most votes for the Bulgarian Sportsperson of the Year award, finishing behind wrestler Ivo Angelov with 1331 points.

2013: Uses Wilson Pro Room Racket

As of 2013, Grigor Dimitrov uses a customized Wilson mid-size 93 square inches prototype racket provided by the Wilson Pro Room Team, cosmetically the Pro Staff 95 BLX, weighted about 12.oz strung with a 16X19 string pattern.

WILSON PRO STAFF SIX ONE 95 18X20 V14 Tennis Racquet

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2013: Brisbane International Final

In 2013, Grigor Dimitrov started his season at the Brisbane International, reaching his first ATP singles final and becoming the first Bulgarian player to achieve this. He lost to Andy Murray despite being a break up in both sets. He also reached the doubles semifinals with Kei Nishikori but withdrew due to Nishikori's injury. His performance resulted in him surpassing $1 million earned in prize money.

2013: Major Unseeded Status

In 2013, Grigor Dimitrov was unseeded at a Major for the first time since.

2013: First Win Against World No. 1 Confirms Relationship

In 2013, after the Madrid Open where Grigor Dimitrov had his first win against a world No. 1, beating Novak Djokovic, he and Maria Sharapova confirmed their relationship.

2013: Masters Quarterfinal Streak

In March 2024 it was noted that with making his 19th Masters quarterfinal in Miami, Grigor Dimitrov reached that stage or higher of at least one Masters event every season for 12 years in a row since 2013.

December 2014: Bulgarian Sportsperson of the Year Award

In December 2014, Grigor Dimitrov was named the Bulgarian Sportsperson of the Year with 1190 points, marking the first time a tennis player had received this honor.

2014: Between-the-Leg Shots

In 2014, Grigor Dimitrov hit successive between-the-leg shots off Jack Sock's returns in the Stockholm Open, which were considered among the best trick shots ever.

2014: Wimbledon Semifinal and Top-10 ATP Ranking

In 2014, Grigor Dimitrov reached the Wimbledon semifinals, defeating defending champion Andy Murray in the quarterfinals. Although he was beaten by Novak Djokovic in the semifinals, this performance led him to enter the top-10 ATP rankings for the first time, at No. 9, becoming the first Bulgarian male tennis player to achieve this milestone.

2014: Sports Icarus Award

In 2014, Grigor Dimitrov received the Sports Icarus Award.

2014: Brisbane International and Kooyong Exhibition

In 2014, Grigor Dimitrov started the season ranked 23rd and participated in the Brisbane International, where he lost to Marin Čilić in the second round. He also competed in the Kooyong exhibition, failing to secure a victory and ultimately withdrawing before the seventh-place playoff.

2014: Switched to 18X17 String Pattern

In 2014, Grigor Dimitrov switched to an 18X17 string pattern on his racket.

2014: Bulgarian Sportsperson of the Year

In 2014, Grigor Dimitrov was named the Bulgarian Sportsperson of the Year.

2014: Last ATP Title at Queen's Club

In 2014, Grigor Dimitrov won his last ATP title at Queen's Club.

February 2015: Return to Top Ten Ranking

In February 2015, Grigor Dimitrov returned to the top ten in the ATP rankings at the conclusion of the tournament.

March 2015: Exhibition Match Victory over Federer

On March 10, 2015, Grigor Dimitrov defeated Roger Federer at an annual exhibition tournament held in Madison Square Garden, marking his first-ever victory against the Swiss player.

July 2015: Separation from Maria Sharapova

In July 2015, Grigor Dimitrov and Maria Sharapova ended their relationship, concluding their highly publicized romance.

July 2015: Parted Ways with Roger Rasheed

On July 7, 2015, Grigor Dimitrov announced that he would be parting ways with coach Roger Rasheed.

September 2015: Hired Franco Davín as Coach

On September 25, 2015, Grigor Dimitrov announced that he had hired Juan Martín del Potro's former coach Franco Davín.

2015: Switched to 97 Square Inches Head Size

From 2015 onwards, Grigor Dimitrov switched to a 97 square inches head size for his racket, similar to Federer's frame but with an 18X17 pattern.

2015: Davis Cup Playoff Victory

In April 2015, Grigor Dimitrov played for the Bulgarian Davis Cup team in the Europe Group II playoffs. He won his singles match and partnered with Dimitar Kutrovsky to win the doubles, securing Bulgaria's position in Europe Group II for 2015.

June 2016: Daniel Vallverdu Becomes Coach

Since June 2016, Grigor Dimitrov has been coached by Daniel Vallverdu.

2016: 2016 Summer Olympics and Cincinnati Masters Semifinal

In 2016, Dimitrov participated in the Summer Olympics, losing in the first round to Marin Čilić. Later in Cincinnati, he reached his third career Masters semifinal, which boosted him back into the top 30 of the ATP rankings.

2016: Coaching Change and Wimbledon Performance

In 2016, Grigor Dimitrov faced early losses in Stuttgart and London. However, he ended his losing streak at Wimbledon. Soon after, he split with his coach Franco Davín and hired Daniel Vallverdu as his new coach.

2016: Double Faults Comparison

In 2016, Grigor Dimitrov made fewer double faults compared to 2017.

2016: Olympic Appearance in Rio

In 2016, Grigor Dimitrov made his second Olympic appearance in Rio, where he was defeated in the first round of the singles competition by Marin Čilić.

2016: Developed Pro Staff 97S with Wilson

In 2016, Grigor Dimitrov worked with the Wilson Pro Room Team to develop the Pro Staff 97S model with a thinner beam width of 19.5mm.

2016: US Open Fourth Round Appearance

In 2016, Grigor Dimitrov, seeded 22nd, reached the fourth round of the US Open for the second time in his career before losing to Andy Murray.

2016: Parted Ways with Franco Davín

In the first half of 2016, Grigor Dimitrov and Franco Davín parted ways.

November 2017: ATP Finals Victory

In November 2017, Grigor Dimitrov won the ATP Finals, which was the biggest title of his career. He then achieved a world No. 3 ranking in singles by the ATP, which made him the highest-ranked Bulgarian in history.

2017: Credited Vallverdu for Upturn in Form

During the 2017 season, Grigor Dimitrov credited Daniel Vallverdu with his upturn in form, particularly his improved mentality against top ten players.

2017: Displayed Backhand Ability Against Nadal

During the Australian Open 2017 semi-final against Rafael Nadal, Grigor Dimitrov displayed his ability to generate significant pace on his backhand more than 50 times.

2017: Significant Milestones in 2017

Grigor Dimitrov ended the 2017 season with several significant milestones, including his first Masters 1000 title, first ATP Finals crown, 5 Tour finals, four tour titles, eight top-10 match wins, 250 career match wins, cracking $10,000,000 in career earnings, cracking $5,000,000 in a single season, second Grand Slam semifinal, and first Grand Slam semifinal on hard courts.

2017: Problem with Double Faults

In 2017, Grigor Dimitrov had a problem with double faults, making 254 of them, which was around 40 more than in 2016, despite it being his best season so far.

2017: Second Bulgarian Sportsperson and Balkan Athlete of the Year Awards

In 2017, Grigor Dimitrov received the Bulgarian Sportsperson of the Year award for the second time, and also secured the Balkan Athlete of the Year award, recognizing his athletic achievements.

2017: Sports Icarus Award

In 2017, Grigor Dimitrov received the Sports Icarus Award.

2017: Brisbane Title and Australian Open Semifinal

In 2017, Grigor Dimitrov started the season strong, winning the Brisbane title and reaching the semifinals of the Australian Open, where he lost a close match to Rafael Nadal.

2017: Balkan Athlete of the Year

In 2017, Grigor Dimitrov was named the Balkan Athlete of the Year.

2017: Bulgarian Sportsperson of the Year

In 2017, Grigor Dimitrov was named the Bulgarian Sportsperson of the Year.

2017: ATP Finals Victory

In 2017, Grigor Dimitrov won the biggest title of his career at the ATP Finals, defeating David Goffin in the final. He finished the tournament undefeated and reached a career-high world No. 3 ranking.

2017: US Open Semifinal Run

In 2017, Grigor Dimitrov, unseeded, had a remarkable run at the US Open, defeating Roger Federer in the quarterfinals to reach his first Grand Slam semifinal since the 2017 Australian Open. He lost to Daniil Medvedev in the semifinals, resulting in a significant ranking jump.

2017: Most top 10 wins since 2017

In 2023 at the China Open, Grigor Dimitrov defeated Holger Rune. It was his fourth top 10 win (the most since the 2017 season).

2017: Paris Masters Final

In 2023 at the Rolex Paris Masters, Grigor Dimitrov reached his first Masters final since 2017, where he lost to Novak Djokovic.

2017: First Title since 2017

In January 2024, Grigor Dimitrov won his ninth title and first since 2017 at the Brisbane International, defeating Holger Rune in the final.

2017: Back-to-back top 5 wins

In March 2024 Grigor Dimitrov reached his third Masters final defeating back to back top 5 players for his first win against Alexander Zverev in 10 years, and his 20th overall against the top 5. The last time he had defeated back-to-back top 5 players was in Brisbane 2017.

October 2018: Highest Ranking in October 2018

In March 2024, Grigor Dimitrov returned to his highest ranking of world No. 12 for the first time since October 29, 2018 when he was ranked at No. 10.

November 2018: Return to Top 10

In March 2024, Grigor Dimitrov returned for the first time in 260 weeks (3rd longest gap in the Open Era) since November 2018 to the top 10 at world No. 9 in the rankings.

2018: First final since 2018

In 2018, Dimitrov Reached his first final since 2018 defeating Taylor Fritz before losing in the final to Nicolás Jarry. Dimitrov reached the fourth round at Roland Garros defeating Timofey Skatov, Emil Ruusuvuori and Daniel Altmaier without losing a set. He lost to Alexander Zverev.

2018: Toronto Masters Quarterfinals and Cincinnati Masters Title Defense Failure

In 2018, Grigor Dimitrov reached the quarterfinals at the Toronto Masters and failed to defend his Masters title in Cincinnati. Consequently, his ranking dropped to world No. 8.

2018: Brisbane and Australian Open Performances and Shoulder Injury

In 2018, Grigor Dimitrov started the season in Brisbane, reaching the semi-finals. He then reached the quarter-finals of the Australian Open. He withdrew from the Sofia Open due to a shoulder injury.

2018: Paris Masters Round of 16

In 2018, at the Paris Masters, Grigor Dimitrov defeated Richard Gasquet and Karen Khachanov in the second round, the last set being 6-0. He then lost to Alexander Zverev in the round of 16.

2018: Rotterdam Open Semifinal

In 2018, at the Rotterdam Open, Grigor Dimitrov reached the second round after defeating Karatsev. He then defeated Hubert Hurkacz. He reached the semifinals defeating Alex de Minaur and returned to the top 25 in the rankings. He lost to Daniil Medvedev.

2018: Highest Singles Ranking since 2018

In January 2024, as a result of winning the Brisbane International, Grigor Dimitrov moved to No. 13 in the singles rankings on January 8, 2024, his highest since 2018.

May 2019: Split with Daniel Vallverdu

On May 7, 2019, Grigor Dimitrov declared that he and Daniel Vallverdu had parted ways after a string of unsuccessful tournament participations.

2019: US Open Semifinal

In 2019, Dimitrov could not defend his points from the US Open semifinal.

2019: Brisbane and Australian Open Performances

In 2019, Grigor Dimitrov started his campaign in Brisbane, losing to Kei Nishikori in the quarterfinals. In January, he reached the last 16 of the Australian Open but was knocked out by Frances Tiafoe.

2019: Won Against Federer at US Open

In 2019, Grigor Dimitrov won one of his eight meetings with Roger Federer, at the US Open.

2019: Relationship with Nicole Scherzinger Ends

In 2019, Grigor Dimitrov's romantic relationship with American singer Nicole Scherzinger, the lead vocalist of The Pussycat Dolls, ended.

2020: Worked with Christian Groh

During 2020, Grigor Dimitrov worked with German coach Christian Groh.

2020: Skipped Tokyo Olympics

In 2020, Grigor Dimitrov skipped the Tokyo Olympics and registered to play at the ATP 250 tournament in Atlanta, but he later withdrew due to not meeting the Davis Cup representation requirements.

2020: First time since 2020 at the Italian Open

In 2024, at the Italian Open, Grigor Dimitrov reached again the round of 16, for the first time since 2020.

2020: ATP Cup Participation and Victories

In January 2020, Grigor Dimitrov led the Bulgarian team in the inaugural ATP Cup, winning his single matches against Great Britain and Moldova, and securing a doubles victory against the British team.

January 2021: Dante Bottini Becomes Coach

Since January 3, 2021, Grigor Dimitrov was coached by Dante Bottini, who replaced Christian Groh.

September 2021: Ranking drop to No. 29

On September 13, 2021, Dimitrov dropped out of the top 25, since he could not defend his points from the 2019 US Open semifinal, to No. 29.

2021: San Diego Open Semifinal

In late September 2021, Grigor Dimitrov had his first win over Márton Fucsovics at the 2021 San Diego Open. He reached his first semifinal of the year defeating Aslan Karatsev and lost to eventual champion Casper Ruud in the semifinals.

2021: Previously wore Air Zoom Vapor X

Prior to 2021, Grigor Dimitrov wore the Nike Air Zoom Vapor X shoes, which were also Roger Federer's shoe of choice.

September 2022: Split with Dante Bottini

In September 2022, Grigor Dimitrov split with his coach, Dante Bottini.

October 2022: Vallverdu Returns as Coach

In October 2022, Daniel Vallverdu agreed to coach Grigor Dimitrov again until the end of the 2022 season.

November 2022: Finishing the Year in Top 30 & Ranking

In November 2022, Grigor Dimitrov finished the year in the top 30 for the tenth year in a row, ranked world No. 28 on November 21, 2022.

November 2022: End of 2022 Season with Vallverdu

The 2022 season, during which Daniel Vallverdu coached Grigor Dimitrov, ended in November 2022.

December 2022: Vallverdu to Coach Dimitrov in 2023

On December 1, 2022, it was confirmed that Daniel Vallverdu would continue to coach Grigor Dimitrov in 2023.

2022: Masters Semifinal

In 2022, at Shanghai, Grigor Dimitrov defeated Carlos Alcaraz, Nicolás Jarry and reached his first Masters semifinal since the 2022 Monte-Carlo Masters. He lost to Andrey Rublev.

2022: 2022 Season Performances

In 2022, at the Canadian Open, Grigor Dimitrov reached the second round in singles and in doubles with Andrey Rublev. At the 2022 Western & Southern Open he also reached the second round in doubles. He won his opening match at the 2022 Erste Bank Open in Vienna against Thiago Monteiro, reached the quarterfinals and then the semifinals, losing to Daniil Medvedev. At the 2022 Rolex Paris Masters he reached the third round.

2022: Reaching 350 Career Wins at Delray Beach Open

In 2022, at the Delray Beach Open, Grigor Dimitrov achieved his 350th career win after defeating Mitchell Krueger, making him the second man born in the ‘90s or later to reach this milestone, after Milos Raonic. He was the 130th man in the Open Era and the 22nd active player to achieve this.

April 2023: Ranking Drop in April 2023

On April 17, 2023, Grigor Dimitrov dropped outside of the top 30 in the rankings, as he was unable to defend his semifinal points from the previous year.

July 2023: Return to Top 20 in July 2023

On July 24, 2023, Grigor Dimitrov returned to the top 20 after reaching the fourth round at the Wimbledon Championships.

November 2023: Return to Top 15 in November 2023

In November 2023, Grigor Dimitrov returned to the top 15, at world No. 14 on November 6, 2023, after reaching his first Masters final since 2017 at the Paris Masters.

2023: Confirmation for United Cup

Based on his ranking, being the Bulgarian male player No. 1, Grigor Dimitrov was confirmed to participate at the 2023 United Cup as part of the Bulgarian team, two days after finishing the year in the top 30 on November 21, 2022.

2023: Became Lacoste Ambassador

From the 2023 French Open onwards, Grigor Dimitrov became an ambassador for Lacoste.

2023: Partnership with Bianchet

In 2023, Grigor Dimitrov entered into a multilevel partnership agreement with Bianchet.

2023: 2023 Australian Open

In 2023, Grigor Dimitrov reached the third round at the Australian Open, defeating Aslan Karatsev and Laslo Djere. He then lost to Novak Djokovic.

2023: 2023 BNP Paribas Open and Miami Open

In 2023, at the BNP Paribas Open, Grigor Dimitrov lost in the second round to Jason Kubler after retiring with a right-knee injury. At the Miami Open, he won his second-round match against Jan-Lennard Struff.

2023: 400th Career Win at Chengdu Open

In 2023, at the Chengdu Open, Grigor Dimitrov recorded his 400th career win defeating Juan Pablo Varillas, becoming the first man born in the 1990s or later to hit that milestone and the tenth active men's player. He reached the semifinals, losing to Alexander Zverev. At the China Open, he won his first-round match against Mackenzie McDonald and then defeated Holger Rune to reach the quarterfinals.

January 2024: Brisbane International Title Win and Ranking Improvement

In January 2024, Grigor Dimitrov won his ninth title and first since 2017 at the Brisbane International, defeating Holger Rune in the final. He moved to No. 13 in the singles rankings on January 8, 2024, his highest since 2018.

March 2024: Return to Highest Ranking and Miami Masters

In March 2024, Grigor Dimitrov reached his highest ranking of world No. 12 on March 18th, for the first time since October 2018. At the Miami Open, he reached the fourth round, later winning against Hubert Hurkacz and thus completing the full career set of quarterfinal showings at all nine active Masters events. He reached his third Masters final, losing to Jannik Sinner. He returned to the top 10 at world No. 9 in the rankings. Dimitrov became just the third man born in 1990 or later to record 40 or more Top 10 wins after Alexander Zverev and Daniil Medvedev and the eight active player overall.

December 2024: Stefan Edberg Sportsmanship Award

In December 2024, Grigor Dimitrov was selected as the winner of the Stefan Edberg Sportsmanship Award, acknowledging his conduct and sportsmanship on and off the court.

2024: Completes Career Set of Grand Slam and Masters 1000 Quarterfinals

In 2024, Grigor Dimitrov reached the French Open quarterfinals and became the second player born in the 1990s (after Daniil Medvedev) to complete the career set of both Grand Slam and Masters 1000 quarterfinals.

2024: 2024 Season Achievements

In 2024, Grigor Dimitrov was selected for Team Europe at the Laver Cup. He reached the round of 16 at the Shanghai Masters, recording his 40th win for the season. He reached his 21st ATP career final at the Stockholm Open, recording his 100th indoor win. At the Rolex Paris Masters, Dimitrov made his 20th Masters quarterfinal of his career.

2024: Miami Open Runner-Up

In 2024, Grigor Dimitrov was the runner-up at the Miami Open, setting the stage for his quarterfinal appearance in the subsequent 2025 tournament.

2024: 2024 Australian Open Participation

In 2024, Grigor Dimitrov, seeded 13th at the Australian Open, made his record 52nd consecutive major appearance. He reached the second round with a win over Marton Fucsovics, won over Kokkinakis in the second round, but lost in the third round to Nuno Borges.

2024: Monte-Carlo Masters and Italian Open

In 2024, at the Monte-Carlo Masters, Grigor Dimitrov played the longest best-of-three match in the tournament's history. At the Italian Open, he reached the round of 16, for the first time since 2020, and lost to Taylor Fritz.

2024: 2024 Wimbledon Championships Comeback

In 2024, at the Wimbledon Championships, Grigor Dimitrov came back from two sets to love deficit for the second time in his career, defeating Shang Juncheng to reach the third round. It was the ninth overall comeback from two sets down in a single edition of the All England Club, tying the record for most comebacks at the tournament in the Open Era.

2025: Longest Active Grand Slam Streak

As of 2025, Grigor Dimitrov holds the distinction of being the male player with the longest active streak of consecutive Grand Slam appearances, totaling 56.

2025: Most Wins at Brisbane International

In 2025, with his first-round win over Yannick Hanfmann at the Brisbane International, Grigor Dimitrov became the player with the most wins in the tournament's history, with a win-loss record of 24-6. He then defeated Aleksandar Vukic to reach the quarterfinals, his 25th record-breaking win at the event.