For the generation of tennis players born in the 1990s, it wasn’t easy to come after the success of ‘the ‘Big Three’. Grigor Dimitrov is a clear example: he has delivered strong results and is still competing at a high level today, but for most of his career, he frequently had to go up against his idols.
Dimitrov was born in Haskovo, a city in Bulgaria located about 230 kilometers from the capital, Sofia. He trained and competed in junior categories until 2008, being ranked World No. 1 and winning two major boys’ singles titles at the 2008 Wimbledon Championships and the 2008 US Open.
At age 17, he began his professional career. Dubbed ‘Baby Fed,’ due to his similarities with Roger Federer, Dimitrov was a promising talent. However, he said he never liked the label. “I never liked it and it never brought me any good. Of course I’m flattered but I always wanted to be my own person,” he told The Athletic in 2024.
As he worked his way up in the circuit, it took him five years to win his first ATP title. In 2014, he broke through, and by 2017 he hit his peak, capturing four titles and reaching a career-high ATP ranking of world No. 3.
Grigor Dimitrov during the Miami Open in 2025 (Brennan Asplen/Getty Images)
Then, after some years struggling to get good results, he had a “renaissance” in 2024, reaching the finals of the Miami Open and Stockholm Open, as well as returning to the Top 10. While the Bulgarian is known for being one of the most friendly guys on the tour, he also had his fair share of off-court gossip.
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The Serena-Sharapova scandal
The Bulgarian is also known for events beyond the tennis court. While his relationship with Maria Sharapova, one of the greatest Russian tennis players of all time, was publicly known, he was also rumored to have dated Serena Williams in 2012.
In 2012, Dimitrov and Williams shared a coach, Patrick Mouratoglou, who was also romantically linked to Williams. The following year, Dimitrov was publicly dating Sharapova and the American made some harsh comments to the press.
Grigor Dimitrov watching Maria Sharapova during the 2014 French Open (Matthew Stockman/Getty Images)
At the time, the 23-time Grand Slam champion told Rolling Stone about Sharapova: “She begins every interview with ‘I’m so happy. I’m so lucky.’ It’s so boring. And, hey, if she wants to be with the guy with a black heart, go for it.“
In response, Sharapova fired back: “If she wants to talk about something personal, maybe she should talk about her relationship and her boyfriend who was married. Not to mention, he’s getting divorced and has kids.”
It’s worth noting that both comments were made in 2013, and that Serena later apologized to Sharapova. In the years since, the three of them, managed to improve their relationship, and the issue was left in the past. Williams has even been seen supporting Dimitrov in several matches, most recently at the US Open in 2024.
Dimitrov and Williams practice together ahead of the Australian Open in 2019 (Michael Dodge/Getty Images)
“A lot has changed,” he told The Athletic about his personal matters. “There comes a point where I had to make some tough decisions on and off the court […] It’s life. For me, part of growing as a human is you have basic experiences, which I didn’t really have, being a tennis player,” he said. “I always wanted to make sure that I did have those things and maybe that’s why at times they were taking me away from the game. But I definitely don’t regret it.”
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Dimitrov vs. the Big Three
Throughout his career, Dimitrov has repeatedly faced the Big Three, and unsurprisingly, his record against them is unfavorable. Against Federer, he played eight times and won only once—in the 2019 US Open quarterfinals. He faced Nadal 15 times and won just once, in the Beijing ATP quarterfinals. Against Djokovic, they’ve played 14 times, with Dimitrov winning only once as well, in the first round of the 2013 Madrid Masters 1000.
Dimitrov and Djokovic during the Paris Open trophy ceremony in 2023 (Dean Mouhtaropoulos/Getty Images)
In 2024, he told The Athletic that the match he lost to Nadal in the Australian Open semifinals in 2017 was one of the losses he regrets the most. “The match with Rafa took me seven or eight months to get over,” Dimitrov said. “There was no way I could lose the match, and yet I lost the match.”
The Impressive Career of Grigor Dimitrov
Now 33, Grigor Dimitrov is still going strong. While it took him years to reach maturity and deliver consistent results, he’s carved out a solid career. His resume includes nine ATP titles, with the most significant being the 2017 ATP Finals, where he defeated David Goffin in three sets. That same year, he climbed to No. 3 in the world.
After his breakthrough in 2017, injuries led to some inconsistency, but in recent years he has returned to prominence, spending most of his time in the top 15 and continuing to compete at a high level.
In Grand Slams, his best results have been semifinal appearances at the Australian Open (2017), Wimbledon (2014), and the US Open (2019). At Roland Garros, his best showing came in 2024 when he reached the quarterfinals.
A new perspective
Despite a career marked by highs and lows both on and off the court, Grigor Dimitrov has stepped out from the shadow of the Big Three to earn his place as one of the most respected players in the game.
“But I think I’m navigating myself better with things, and I also know that at the moment I’m way closer to the end than the beginning, and that also gives you a very different perspective,” he told The Athletic.
Grigor Dimitrov in 2023 (Getty Images)
So, while he might not be able to match the Grand Slam totals of Federer, Nadal or Djokovic, Dimitrov has carved out a legacy of his own. With a renewed perspective and steady presence on the tour, he remains a player capable of captivating crowds and challenging the best.
