History of Grigor Dimitrov in Timeline

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Grigor Dimitrov

Grigor Dimitrov is a highly accomplished Bulgarian professional tennis player. His career-high ranking is world No. 3, the highest ever achieved by a Bulgarian player. Dimitrov's most significant victory came at the 2017 ATP Finals. He has secured nine ATP Tour singles titles throughout his career.

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1958: Creation of Bulgarian Sportsperson of the Year Award

In 1958, the Bulgarian Sportsperson of the Year award was created.

1974: Wimbledon Comeback Record

At the 2024 Wimbledon Championships, Dimitrov had a comeback 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 (with 1974, 1990 and 1997) for most comebacks at the tournament in the Open Era.

1990: Wimbledon Comeback Record

At the 2024 Wimbledon Championships, Dimitrov had a comeback 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 (with 1974, 1990 and 1997) for most comebacks at the tournament in the Open Era.

1990: 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 1990 or later to reach this milestone and the tenth active men's player.

1990: 100th Indoor Win

In 2024, With reaching the semifinals at the 2024 Stockholm Open, Dimitrov recorded his 100th indoor win over Dominic Stricker, becoming the first man born in the 1990 or later to accomplish the feat.

1990: Miami Masters Semifinal

In March 2024, 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 with his 40th top 10 win over Carlos Alcaraz in the quarterfinals.

May 1991: Grigor Dimitrov's birth

In May 1991, Grigor Dimitrov was born in Bulgaria.

1991: Birth of Grigor Dimitrov

In 1991, Grigor Dimitrov was born in Haskovo, Bulgaria, to Dimitar Dimitrov, a tennis coach, and Maria Dimitrova, a sports teacher.

1997: Wimbledon Comeback Record

At the 2024 Wimbledon Championships, Dimitrov had a comeback 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 (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 recognized 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 title.

2007: Joins Sanchez-Casal academy

In 2007, Grigor Dimitrov joined the "Sanchez-Casal" academy for further training.

2007: Orange Bowl Finalist and US Open Doubles Final

In 2007, Grigor Dimitrov was a finalist at the Orange Bowl U18 boys singles and reached the US Open doubles final with Vasek Pospisil.

2007: Eddie Herr International Rising Star

In 2007, Grigor Dimitrov was named the Eddie Herr International Rising Star.

2008: Post-Wimbledon 2008 performances

After winning US Open boys tournament as the 2008 winner, Grigor received a wildcard for the US Open qualification tournament, where he lost in the second round. He also won his first doubles Challenger title at the ATP Challenger Trophy.

2008: Wimbledon Debut and Injury

At his Grand Slam debut at Wimbledon in 2008, Grigor Dimitrov retired due to a knee injury during his first-round match against Igor Kunitsyn, despite winning the first set.

2008: Transition to Men's Events and First ATP Level Win

In 2008, Grigor Dimitrov began participating in men's events, winning his first title on clay in Barcelona and securing his first ATP level win at the Swiss Indoors.

2008: Junior Grand Slam Success and World No. 1 Ranking

In 2008, Grigor Dimitrov won Wimbledon and the US Open junior titles, and on September 8, 2008, became junior world No. 1. He also reached the French Open quarterfinals.

2008: Junior Grand Slam wins

In 2008, Grigor Dimitrov won the boys' singles titles at Wimbledon and the US Open during his junior career.

2008: Davis Cup Debut for Bulgaria

In 2008, at age 16, Grigor Dimitrov debuted for Bulgaria in the Davis Cup. Playing in Plovdiv, he had an undefeated record in singles and doubles, which led to Bulgaria's promotion into the second division of the Europe/Africa zone.

March 2009: Training in Paris

In March 2009, Grigor Dimitrov began training at Patrick Mouratoglou's tennis academy in Paris, France.

2009: Coaching Relationship with Peter Lundgren

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

2009: Davis Cup Victory Over Hungary

In 2009, 17-year-old Grigor Dimitrov returned to the Bulgarian Davis Cup team for the first round of the Davis Cup Europe/Africa zone. Dimitrov won both of his singles matches, contributing to a 3–2 victory over Hungary.

2009: Wimbledon Main Draw Entry

In 2009, Grigor Dimitrov earned a wildcard entry into the Wimbledon men's draw due to his junior Wimbledon victory.

2009: First ATP Tour Main-Draw Win

In 2009, Grigor Dimitrov upset Tomáš Berdych at the Rotterdam Open, securing his first ATP Tour main-draw win.

June 2010: Ended Coaching Relationship with Lundgren

In June 2010, Grigor Dimitrov ended his coaching relationship with Peter Lundgren and began being coached by Peter McNamara.

2010: Sponsored by Nike

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

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

2011: End of Coaching Relationship with McNamara

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

November 2012: Joins 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 ex-touring pros Magnus Norman, Nicklas Kulti, and Mikael Tillström.

2012: 2012 Wimbledon Championships

At the 2012 Wimbledon Championships, Dimitrov won his first-round match against Kevin Anderson but retired in the second round due to an injury.

2012: Hopman Cup and win against top 10 player

During the 2012 Hopman Cup, Grigor Dimitrov beat Mardy Fish in straight sets; his first win against a top 10 player, though not an official ATP win.

2012: 2012 Season Wrap-up

In 2012, Dimitrov reached the quarterfinals at the Swiss Indoors Basel, losing to Paul-Henri Mathieu. At the Paris Masters, he beat Jürgen Melzer. He ended the year ranked world No. 48 in singles.

2012: Semifinal Appearances at Swedish Open and Suisse Open Gstaad

In 2012, Dimitrov reached the semi-finals of both the Swedish Open and the Suisse Open Gstaad losing to David Ferrer and Thomaz Bellucci respectively.

2012: Patrick Mouratoglou as Coach

In 2012, Grigor Dimitrov appointed Patrick Mouratoglou as his coach.

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 for the first time. He won his first-round match against Łukasz Kubot but was then defeated by Gilles Simon.

2012: Return to Davis Cup Competition

In 2012, Grigor Dimitrov returned to Davis Cup competition as a top 100 player. The Bulgarian team had a successful round-robin tournament in Sofia and was promoted to the second division of the Europe/Africa zone once again.

2012: Dating Maria Sharapova

In late 2012, Grigor Dimitrov began dating Maria Sharapova.

October 2013: First ATP Title

In October 2013, Grigor Dimitrov won his first ATP Tour singles title at the Stockholm Open, becoming the first Bulgarian man to achieve this.

October 2013: Hiring Roger Rasheed as New Coach

On October 7, 2013, Grigor Dimitrov announced that he had hired Roger Rasheed as his new coach. Rasheed had previously coached Gaël Monfils, Jo-Wilfried Tsonga, and Lleyton Hewitt.

December 2013: Bulgarian Sportsperson of the Year Award runner-up

In December 2013, Grigor Dimitrov finished second in the voting for the Bulgarian Sportsperson of the Year award.

2013: First win against world No. 1

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

2013: Using Wilson Pro Staff 95 BLX Racket

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

WILSON PRO STAFF SIX ONE 95 18X20 V14 Tennis Racquet
WILSON PRO STAFF SIX ONE 95 18X20 V14 Tennis Racquet

2013: First ATP Singles Final

In 2013, Dimitrov reached his first ATP singles final at the Brisbane International, becoming the first Bulgarian player to achieve this milestone, but lost to Andy Murray.

2013: Miami Masters Quarterfinal

In March 2024, Dimitrov made his 19th Masters quarterfinal in Miami, he 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

In December 2014, Grigor Dimitrov was chosen as the Bulgarian Sportsperson of the Year, earning 1190 points and becoming the first tennis player to win the award.

2014: Wimbledon Semifinal and Top 10 Ranking

At the 2014 Wimbledon Championships, Grigor Dimitrov reached his first Grand Slam semifinal, becoming the first male Bulgarian player to do so. He also entered the top-10 ATP rankings for the first time, at No. 9.

2014: Between-the-Leg Shots

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

2014: Brisbane International performance

In 2014, Grigor Dimitrov participated in the Brisbane International. While he won his first-round match, he lost in the second round. He also competed in the doubles, losing in the second round.

2014: Sports Icarus Award

In 2014, Grigor Dimitrov received the Sports Icarus Award.

2014: Switching to 18X17 String Pattern

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

2014: Bulgarian Sportsperson of the Year

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

March 2015: Exhibition Match Win Against Federer

On 10 March 2015, Grigor Dimitrov played at an annual exhibition tournament in Madison Square Garden against Roger Federer, defeating the Swiss star for the first time.

July 2015: Separation from Sharapova

In July 2015, Grigor Dimitrov and Maria Sharapova separated.

July 2015: Parting Ways with Coach Roger Rasheed

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

September 2015: Hiring Franco Davín as Coach

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

2015: Switching to 97 Square Inches Head Size

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

2015: Davis Cup Europe Group II Playoffs

In April 2015, Grigor Dimitrov played for Bulgaria in the Davis Cup Europe Group II playoffs, securing a 3-0 lead against Greece and maintaining Bulgaria's position in Group II for 2015.

June 2016: Coached by Daniel Vallverdu

Since June 2016, Grigor Dimitrov has been coached by Daniel Vallverdu, a former coach of Andy Murray.

2016: Hired Daniel Vallverdu as coach

In 2016, Grigor Dimitrov hired Daniel Vallverdu as his coach after splitting with Franco Davín prior to Wimbledon.

2016: Double Faults Comparison

In 2016, Grigor Dimitrov made approximately 40 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: Reached Semifinal in Cincinnati Masters

In 2016, Grigor Dimitrov participated in the Summer Olympics and reached his third career Masters semifinal in Cincinnati, securing the second spot in the 2016 US Open Series standings and returning to the top 30 of ATP ranking.

2016: Developing Pro Staff 97S Model

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: Reached Fourth Round at US Open

In 2016, seeded 22nd, Grigor Dimitrov played in the US Open and reached the fourth round for a second time in his career.

2016: Parting Ways with Franco Davín

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

November 2017: ATP Finals victory

In November 2017, Grigor Dimitrov won the ATP Finals, marking the biggest title of his career and propelling him to a world No. 3 ranking.

2017: Reached US Open Semifinals After Upsetting Federer

At the US Open in 2017, Grigor Dimitrov, unseeded, upset Roger Federer in a five-set match to reach his first Grand Slam semifinal since the 2017 Australian Open. He then lost to Daniil Medvedev in the semifinals.

2017: Crediting Vallverdu for Upturn in Form

During the 2017 season, Grigor Dimitrov credited his coach, Daniel Vallverdu, with his improved form, acknowledging Vallverdu's impact on his mentality and playstyle against top ten players, particularly after winning the 2017 ATP Finals.

2017: Significant Milestones in 2017 Season

Grigor Dimitrov ended his 2017 season with 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: Double Fault Problem

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

2017: Sports Icarus Award

In 2017, Grigor Dimitrov received the Sports Icarus Award.

2017: Balkan Athlete of the Year

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

2017: Bulgarian Sportsperson of the Year

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

2017: Won First ATP Title in Brisbane

In 2017, Grigor Dimitrov won his first ATP title in nearly three years at Brisbane, defeating Kei Nishikori in the final. He extended his winning streak at the Australian Open, reaching the semifinals.

2017: Bulgarian Sportsperson and Balkan Athlete of the Year

In 2017, Grigor Dimitrov won the Bulgarian Sportsperson of the Year award for the second time and was also named Balkan Athlete of the Year.

2017: Won ATP Finals Title

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

2017: Australian Open Semifinal Against Rafael Nadal

In 2017, during his semifinal match against Rafael Nadal at the Australian Open, Grigor Dimitrov displayed his ability to generate significant pace on his backhand more than 50 times.

2017: China Open of the Asian swing

In 2023, Dimitrov defeated third seed Holger Rune for his fourth top 10 win to reach the quarterfinals of the China Open of the Asian swing (the most since the 2017 season)

2017: First Masters Final Since 2017

In 2023, after a good form on the European indoor hardcourts, Dimitrov reached his first Masters final since 2017, where he lost to Novak Djokovic.

2017: Brisbane International Title

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

2017: Brisbane 2017

In March 2024, Dimitrov reached his third Masters final defeating back to back top 5 players (last time was in Brisbane 2017), for his first win against fourth seed Alexander Zverev in 10 years, and 20th overall against the top 5.

October 2018: Highest Ranking of World No. 10

In March 2024, Grigor Dimitrov returned to his highest ranking of world No. 12 on 18 March 2024 for the first time since 29 October 2018 when he was ranked at No. 10 after reaching the fourth round in Indian Wells.

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: Ranking Dropped to World No. 8

In 2018, Grigor Dimitrov failed to defend his Masters title in Cincinnati and was eliminated in the first round of the US Open, causing his ranking to drop to world No. 8.

2018: Lost in Australian Open Quarterfinal, Withdrew from Sofia Open

In 2018, Grigor Dimitrov lost to Kyle Edmund in the Australian Open quarter-final and later withdrew from the Sofia Open due to a shoulder injury.

2018: First Final Since 2018

In 2018, after winning his first two rounds matches against Roberto Carballés Baena and Christopher O'Connell to reach the semifinals, Grigor 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 for the second time at this major, losing to Alexander Zverev.

2018: Paris Masters

In 2018, at the Paris Masters, Grigor Dimitrov defeated Richard Gasquet and Karen Khachanov in the second round, winning the last set against Khachanov 6-0. However, he 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 Aslan Karatsev. He then defeated Hubert Hurkacz to reach the quarterfinals and Alex de Minaur to reach the semifinals for the first time since 2018 at this tournament, resulting in his return to the top 25 in the rankings. He lost to Daniil Medvedev in the semi-finals.

May 2019: Parting Ways with Vallverdu

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

2019: Victory Over Roger Federer at US Open

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

2019: End of relationship with Nicole Scherzinger

In 2019, Grigor Dimitrov's romantic relationship with Nicole Scherzinger ended.

2019: Reached Last 16 of Australian Open

In January 2019, Grigor Dimitrov reached the last 16 of the Australian Open, but was knocked out by Frances Tiafoe.

2020: Dimitrov worked with Christian Groh

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

2020: Skipping Tokyo Olympics

In 2020, Grigor Dimitrov chose to skip the Tokyo Olympics. He had registered to play at the ATP 250 tournament in Atlanta instead but had to withdraw because he did not meet the minimal qualifications requirements due to non-representation in the Davis Cup.

2020: 2024 Italian Open

In 2024, at the Italian Open he reached again the round of 16, for the first time since 2020 at this Masters

2020: ATP Cup Participation and Victory Over Great Britain

In January 2020, Grigor Dimitrov led the Bulgarian team in the inaugural ATP Cup, winning his single match against Dan Evans of Great Britain and also pulling a victory in doubles against the British pair of Jamie Murray and Joe Salisbury.

January 2021: Dimitrov Coached by Dante Bottini

Since January 3, 2021, Grigor Dimitrov was coached by Dante Bottini, who replaced Christian Groh, Dimitrov's coach during 2020. Bottini is known for coaching Kei Nishikori, who reached number 4 in the world rankings.

September 2021: Ranking Dropped to No. 29

On 13 September 2021, Grigor Dimitrov's ranking dropped out of the top 25 to No. 29 after failing to defend his points from the 2019 US Open semifinal.

2021: Reached Semifinal at San Diego Open

In 2021, Grigor Dimitrov reached his first semifinal of the year at the San Diego Open, defeating Aslan Karatsev before losing to Casper Ruud.

2021: Wore Air Zoom Vapor X

Until 2021, Grigor Dimitrov wore the Nike Air Zoom Vapor X which was 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 Agrees to Coach Dimitrov Again

In October 2022, after parting ways with Wawrinka, Daniel Vallverdu agreed to coach Grigor Dimitrov again until the end of the 2022 season.

November 2022: End of 2022 Season

Grigor Dimitrov's 2022 season ended in November 2022.

November 2022: Finishing the Year Ranked World No. 28

On November 21, 2022, Grigor Dimitrov finished the year ranked world No. 28, marking his tenth consecutive year in the top 30. As the top-ranked Bulgarian male player, he was confirmed on November 23, 2022, as a participant in the 2023 United Cup as part of the Bulgarian team.

December 2022: Vallverdu to Work with Dimitrov in 2023

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

2022: Canadian Open and Vienna Open

In 2022, at the Canadian Open, Grigor Dimitrov reached the second round in singles and in doubles with Andrey Rublev. Following losses at the Sofia and Stockholm Opens, he won his opening match at the Vienna Open against Thiago Monteiro, later defeating Andrey Rublev to reach the quarterfinals and Marcos Giron to reach the semifinals before losing to Daniil Medvedev. At the Rolex Paris Masters he reached the third round.

2022: Delray Beach Open: Dimitrov Achieves Milestone

In 2022, at the Delray Beach Open, Grigor Dimitrov secured his 350th career win after defeating Mitchell Krueger, making him only the second man born in the 1990s or later to reach this milestone, following Milos Raonic. He became the 130th man in the Open Era and the 22nd active player to achieve this.

2022: Masters Semifinal Since Monte-Carlo Masters

In 2023, at Shanghai, Grigor Dimitrov reached the quarterfinals of a Masters 1000 for the first time in the season and only the second time at this Masters. He defeated Nicolás Jarry and reached his first Masters semifinal since the 2022 Monte-Carlo Masters.

April 2023: Ranking Drop After Monte-Carlo Masters

On April 17, 2023, Grigor Dimitrov dropped outside of the top 30 in the rankings, unable to defend his semifinal points from the previous year, following his first round loss to Jiri Lehecka at Monte-Carlo. In Madrid, he defeated Grégoire Barrère before losing to Carlos Alcaraz, and in Rome, he defeated Stan Wawrinka before also losing to Novak Djokovic.

July 2023: Return to Top 20

On July 24, 2023, Grigor Dimitrov returned to the top 20 in the rankings, following his performance at the Queen's Club Championships where he reached the quarterfinals, and at the Wimbledon Championships where he reached the fourth round.

November 2023: Return to Top 15

On November 6, 2023, as a result of reaching his first Masters final since 2017 at the Paris Masters where he lost to Novak Djokovic, Grigor Dimitrov returned to the top 15 in the world rankings, at world No. 14.

2023: Confirmed Participant at the United Cup

Based on his ranking, being the Bulgarian male player No. 1, Grigor Dimitrov was confirmed as a participant at the 2023 United Cup as part of the Bulgarian team.

2023: Became an ambassador for Lacoste

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

2023: Daniel Vallverdu continues to coach Grigor Dimitrov

In 2023, Daniel Vallverdu continued to coach Grigor Dimitrov.

2023: Partnerships with Lacoste and Bianchet

In 2023, Grigor Dimitrov concluded a deal with Lacoste Apparel Products and Lacoste Accessories and entered into a multilevel partnership agreement with Bianchet, adding to his existing endorsements with Nike and Wilson Sporting Goods.

2023: Australian Open

In 2023, Grigor Dimitrov reached the third round at the Australian Open, defeating Aslan Karatsev and Laslo Djere before losing to Novak Djokovic, who went on to win his 10th Australian Open and 22nd Grand Slam.

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 due to a right-knee injury in the third set. 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 reach this milestone and the tenth active men's player. He reached the semifinals but lost to Alexander Zverev. At the China Open, he won his first-round match against Mackenzie McDonald and defeated Holger Rune to reach the quarterfinals.

January 2024: Brisbane International Title

In January 2024, Grigor Dimitrov won his ninth title and first since 2017 at the Brisbane International, defeating Holger Rune in the final. He recorded more match wins (23) than any other player at the tournament. As a result, he moved to No. 13 in the singles rankings on January 8, 2024, his highest since 2018.

March 2024: Return to World No. 12 and Miami Masters Semifinal

In March 2024, Grigor Dimitrov reached his highest ranking of world No. 12 for the first time since October 2018 after reaching the fourth round in Indian Wells. At the Miami Open, he reached the semifinals and secured his 40th top 10 win over Carlos Alcaraz, becoming the third man born in 1990 or later to achieve this. Dimitrov reached his third Masters final, for his first win against Alexander Zverev in 10 years, but lost to Jannik Sinner. As a result, he returned to the top 10 at world No. 9 in the rankings.

December 2024: Stefan Edberg Sportsmanship Award

In December 2024, Grigor Dimitrov was selected as the winner of the Stefan Edberg Sportsmanship Award.

2024: Wimbledon Comeback

At the 2024 Wimbledon Championships, Dimitrov had a comeback 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.

2024: Career Grand Slam and Masters 1000 Quarterfinals

By reaching the 2024 French Open quarterfinals, Grigor Dimitrov completed the career set of Grand Slam and Masters 1000 quarterfinals.

2024: 40th Win

In 2024, Dimitrov recorded his 40th win for the season defeating Alexei Popyrin, to reach the round of 16 at the Shanghai Masters. With reaching the semifinals at the Stockholm Open, he recorded his 100th indoor win over Dominic Stricker, becoming the first man born in the 1990 or later to accomplish the feat. At the Rolex Paris Masters Dimitrov moved ahead of Roger Federer and tied with Pete Sampras and Marat Safin for fourth all-time record wins at the tournament with 24. He lost to Karen Khachanov in straight sets.

2024: Miami Open Runner-Up

In 2024, Grigor Dimitrov was the runner-up at the Miami Open.

2024: Monte-Carlo and Italian Open

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

2024: Current Through 2024 US Open

The information is current through the 2024 US Open.

2025: Longest Active Grand Slam Streak

As of 2025, Grigor Dimitrov holds the record for the longest active streak of consecutive Grand Slam appearances at 56.

2025: Miami Open Quarterfinals and Semifinals

In 2025, at the Miami Open, Grigor Dimitrov reached the quarterfinals, defeating Karen Khachanov and Brandon Nakashima. He then advanced to the semifinals, overcoming Francisco Cerúndolo in a three-set match where he saved a match point.

2025: Most Wins in Brisbane International History

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 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.