Grigor Dimitrov
Bulgarian tennis player
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| April 2025 | Began relationship with Mexican actress Eiza González, confirmed through a shared Instagram post. |
| 2025 | Reached the quarterfinals at the 2025 Miami Open, defeating 22nd seed Karen Khachanov and 31st seed Brandon Nakashima while defending his runner-up points from 2024. |
| 2025 | In the first round of the Brisbane International, Dimitrov won against Yannick Hanfmann, becoming the player with the most wins in the tournament's history. |
| 2025 | Dimitrov advanced to the quarterfinals of the Brisbane International by defeating home favorite Aleksandar Vukic, marking his record-breaking 25th win at the event. |
| 2024 | At the US Open, Dimitrov recorded his 450th career win after defeating sixth seed Andrey Rublev in five sets, marking his second quarterfinal appearance at the Grand Slam and eighth overall. |
| 2024 | At the Rolex Paris Masters, Dimitrov made his 20th Masters quarterfinal of his career, maintaining his chances to qualify for the ATP Finals in Turin. |
| 2024 | Dimitrov reached his 21st ATP career final at the Rolex Paris Masters, defeating seventh seed Tallon Griekspoor but lost to Karen Khachanov. |
| 2024 | At the US Open, he recorded straight sets wins to reach the round of 16 for the third consecutive Grand Slam of the season and defeated sixth seed Andrey Rublev in five sets for his 450th career win. |
| 2024 | Dimitrov reached the final of the Miami Open, becoming the first Bulgarian to complete the full career set of quarterfinal showings at all nine active Masters events. |
| 2024 | During the Wimbledon Championships, Dimitrov staged a comeback from a two sets to love deficit against Shang Juncheng to reach the third round. |
| 2024 | Dimitrov reached his third Masters final after defeating back-to-back top 5 players, marking his first win against fourth seed Alexander Zverev in 10 years; however, he lost in straight sets to world No. 3 Jannik Sinner. |
| 2024 | Dimitrov was selected as part of the winning team Europe at the Laver Cup for the second time. |
| 2024 | He reached the semifinals at the Stockholm Open, marking his 100th indoor win over Dominic Stricker, becoming the first man born in the 1990s to achieve this. |
| 2024 | Dimitrov played the longest best-of-three match in Monte-Carlo Masters history against seventh seed Holger Rune, lasting three and a half hours, but lost in the round of 16. |
| 2024 | Dimitrov reached the quarterfinals of the French Open, becoming the second player born in the 1990s to complete the career set of both Grand Slam and Masters 1000 quarterfinals. |
| 2024 | At Paris Masters, moves ahead of Roger Federer and ties Pete Sampras and Marat Safin for fourth all-time record wins at the tournament with 24. |
| 2024 | Dimitrov wins 1 ATP title and reaches 2 finals, maintaining a strong competitive position at world ranking #11 |
| 2024 | Dimitrov showed strong form with 12th at Australian Open, 10th at French Open and Wimbledon, and 9th at US Open. |
| 2024 | Competed in Laver Cup in Berlin, winning his singles match against Alejandro Tabilo 7–6(7–4), 7–6(7–2) on Day 1, earning 1 point for Team Europe. |
| December 2024 | Dimitrov was selected the winner of the Stefan Edberg Sportsmanship Award. |
| March 2024 | Returned to the top 10 at world No. 9 for the first time in 260 weeks (since November 2018) after reaching the Miami Open final, losing to Jannik Sinner. |
| March 2024 | At the Miami Open, Dimitrov recorded his 40th top 10 win over world No. 2 Carlos Alcaraz in the quarterfinals, reaching the semifinals and completing a full career set of quarterfinal showings at all nine active Masters events. |
| March 18 2024 | Dimitrov returned to his highest ranking of world No. 12, achieving this for the first time since October 29, 2018, following his performance at Indian Wells. |
| January 2024 | Grigor Dimitrov started the season at the Brisbane International, where he reached his third final, defeating Andy Murray, Daniel Altmaier, Rinky Hijikata, and Jordan Thompson. He won the final against top seed Holger Rune, marking his ninth career title and first since 2017. |
| January 8 2024 | Following his victory at Brisbane, Dimitrov moved to No. 13 in the singles rankings, his highest position since 2018. |
| 2023 | Reached quarter-final at the French Open, demonstrating continued competitiveness in major tournaments. |
| 2023 | Dimitrov reached the quarterfinals at the Shanghai Masters after defeating Carlos Alcaraz, marking his first Masters quarterfinal of the season. |
| 2023 | Dimitrov reached the quarterfinals of the China Open by defeating Holger Rune, marking his fourth top 10 win of the season. |
| 2023 | Dimitrov entered into a multilevel partnership agreement with Bianchet. |
| 2023 | During the US Open, Dimitrov won his second-round match against Alex Molcan after coming from behind, saving three match points, and reached the third round by defeating Andy Murray. |
| 2023 | At the Washington Open, Dimitrov reached the semifinals after a walkover from Ugo Humbert but lost to Dan Evans. |
| 2023 | Grigor Dimitrov concluded a deal with Lacoste Apparel Products and Lacoste Accessories. |
| 2023 | Dimitrov recorded his 400th career win at the Chengdu Open, defeating Juan Pablo Varillas, making him the first man born in the 1990s to achieve this milestone. |
| 2023 | Dimitrov reached his first Masters final since 2017 by defeating Stefanos Tsitsipas but lost to Novak Djokovic, resulting in his return to the ATP top 15. |
| 2023 | Dimitrov qualified for the main draw at the Queen's Club Championships, reached the quarterfinals without dropping a set, but lost to Carlos Alcaraz. |
| 2023 | In the Shanghai Masters, Dimitrov defeated Carlos Alcaraz to reach the quarterfinals and subsequently reached his first Masters semifinal of the year. |
| 2023 | Reached final at the Paris Masters, demonstrating continued competitive performance. |
| November 2023 | Dimitrov became the 19th male tennis player ever to win $25 million in prize money. |
| November 6 2023 | Dimitrov returned to the top 15, achieving a ranking of world No. 14 after his performance at the final in Paris. |
| November 6 2023 | Dimitrov returned to the ATP top 15, ranked 14th in the world. |
| July 24 2023 | Dimitrov returned to the top 20 in the ATP rankings after reaching the fourth round of Wimbledon, where he defeated Frances Tiafoe before losing to Holger Rune. |
| July 24 2023 | Dimitrov returned to the top 20 in the ATP rankings after reaching the fourth round at Wimbledon, where he defeated Frances Tiafoe. |
| May 2023 | In Geneva, Dimitrov won his first two matches against Roberto Carballés Baena and Christopher O'Connell to reach the semifinals, where he defeated Taylor Fritz to reach his first final since 2018. |
| May 2023 | At the Geneva Open, Dimitrov reached his first final since 2018 after defeating Taylor Fritz but lost to Nicolás Jarry. |
| May 2023 | Dimitrov reached the fourth round of Roland Garros for the second time, defeating Timofey Skatov, Emil Ruusuvuori, and Daniel Altmaier without losing a set, before losing to Alexander Zverev. |
| April 17 2023 | Dimitrov dropped outside of the top 30 in the rankings after losing in the second round in Monte-Carlo. |
| March 2023 | Dimitrov lost in the second round of the BNP Paribas Open in Indian Wells to Jason Kubler after retiring due to a right-knee injury. |
| February 2023 | At the Rotterdam Open, Dimitrov defeated Aslan Karatsev again to reach the second round, then overcame world No. 10 Hubert Hurkacz to advance to the quarterfinals, and subsequently defeated Alex de Minaur to reach his 43rd career semifinal. |
| January 2023 | Grigor Dimitrov reached the third round of the Australian Open, defeating Aslan Karatsev and Laslo Djere before losing to Novak Djokovic. |
| 2022 | At the Delray Beach Open, Dimitrov recorded his 350th career win after defeating Mitchell Krueger in the second round, becoming only the second man born in the ‘90s or later to achieve this milestone. |
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