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Professional tennis is full of trailblazers, but Grigor Dimitrov is the rare player who's broken new ground in two different ways—for his home country of Bulgaria, and for the cohort of men’s players born in the 1990s.

Here are five ways the 30-year-old has raised the bar in his career, so far:

He was the first man born in 1990 or later to win a title at the ATP Finals level or higher. The 1991-born Dimitrov won the 2017 ATP Finals in London undefeated, becoming the first debutant to go 5-0 en route to the title at the season-ending event since John McEnroe in 1978.

He was the first—and still the only—Bulgarian man to even win an ATP title at any level. He’s won eight career ATP titles so far, the biggest one being the aforementioned ATP Finals title in 2017, followed by one Masters 1000 crown at Cincinnati in 2017 and an ATP 500 title at Acapulco in 2014.

He’s the only Bulgarian man to have reached the semifinals of a Grand Slam. And he’s done it three times, at Wimbledon in 2014 (falling to Novak Djokovic), the Australian Open in 2017 (falling to Rafael Nadal) and the US Open in 2019 (falling to Daniil Medvedev).

He’s the only Bulgarian man in ATP rankings history to break into the Top 10. And he’s been as high as No. 3, reaching that career-high on November 20th, 2017, after his ATP Finals triumph.

He has the second-most career wins of any man born in 1990 or later. With 358 tour-level wins to his name, he only trails 2016 Wimbledon finalist and fellow former No. 3 Milos Raonic, who’s 14 wins ahead at 372. Raonic was born in 1990.

Dimitrov is also in fourth place for most Top 10 wins for a man born in 1990 or later with 29 career wins over the elite, the biggest of which coming against a No. 1-ranked Djokovic at Madrid in 2013. Only Alexander Zverev, Dominic Thiem and Raonic lead Dimitrov in that stat.

Dimitrov is also a former junior No. 1, winning back-to-back junior Slams at Wimbledon and the US Open in 2008.

Dimitrov is also a former junior No. 1, winning back-to-back junior Slams at Wimbledon and the US Open in 2008.

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Dimitrov isn’t showing any signs of slowing down, either.

He’s reached the quarterfinals or better at three of the last five Masters 1000 events, making it to the semifinals of the fall edition of Indian Wells last October, and then the quarterfinals of Indian Wells and semifinals of Monte Carlo already this year.

And after dipping to No. 37 on the ATP rankings at the end of February this year, his lowest ranking since 2019, Dimitrov has bounced right back up, cutting his ranking to No. 22 over the last eight weeks. With less than 250 points dropping off his ranking through the end of the clay-court season, a return to the Top 20 seems likely.

“I have been doing a lot of work on a daily basis, just taking one match at a time,” he said during his run to the final four in Monte Carlo two weeks ago.

“I knew if I put the right amount of work and I kept on following a little bit of what I had to do, good things will happen.”