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Jannik Sinner has advanced to the semifinals of Rotterdam after a 7-6 (4), 1-1 retirement victory over an injured Milos Raonic.

And despite the abbreviated finish to the match, it was a milestone victory for Sinner: the 200th tour-level win of his career, making him the first man born in the 2000s to hit that number.

MOST CAREER WINS, MEN BORN IN 2000s (tour-level):
200: Jannik Sinner, ITA [200-74]
189: Felix Auger-Aliassime, CAN [189-127]
160: Carlos Alcaraz, ESP [160-44]
102: Holger Rune, DEN [102-66]
100: Sebastian Korda, USA [100-65]

Auger-Aliassime and Korda were born in 2000, Sinner was born in 2001 and Alcaraz and Rune were both born in 2003.

And there’s more: the 22-year-old Sinner is also just the seventh Italian man in the Open Era to reach 200 career wins.

MOST CAREER WINS, ITALIAN MEN (tour-level, Open Era):
414: Fabio Fognini [414-375]
395: Adriano Panatta [395-247]
386: Andreas Seppi [386-422]
320: Corrado Barazzutti [320-231]
223: Renzo Furlan [223-239]
219: Andrea Gaudenzi [219-231]
200: Jannik Sinner [200-74]

Sinner will now face Dutch No. 1 Tallon Griekspoor in the semifinals of the ATP 500 event on Saturday.

Sinner will now face Dutch No. 1 Tallon Griekspoor in the semifinals of the ATP 500 event on Saturday.

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It was actually shaping up to be a close one between Sinner and Raonic on Friday night—Sinner was originally up an early break in the first set but Raonic broke right back, and even brought up double set point with the Italian serving at 4-5, 15-40.

But Sinner saved them both—including one with a big forehand winner—and eventually snuck out the first set on a tie-break.

After a pair of holds in the second set it was all over though as Raonic, who had called for a medical time-out early in the first set, ended up retiring from the match after 65 minutes.

“For sure one of the toughest opponents to play against,” Sinner said of Raonic in his on-court interview. “This is a very unusual challenge you have on court. He serves incredibly well, and I was up a break first set and I missed a couple of things—from the last two rounds I was struggling to find myself a little bit on the court, and today I actually felt like he was playing better than me in the first set. I just tried to stay there somehow, mentally.

“But at the end of the day this is not how you want to win this match. He’s had so many injuries throughout his career, and hopefully he’s going to have a speedy recovery.”

Awaiting Sinner in the semifinals of the ATP 500 indoor event will be Dutch No. 1 Tallon Griekspoor, a 7-5, 7-6 (4) quarterfinal winner earlier in the day against Finland’s Emil Ruusuvuori.

Sinner has won both previous meetings with Griekspoor, both of those coming last year, a 7-5, 7-6 (5) victory exactly a year ago in the Rotterdam semifinals, and then a 7-6 (3), 6-1 triumph in the Davis Cup quarterfinals at the end of the year.