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On April 2, 2012, Grigor Dimitrov reentered the Top 100 on the ATP rankings after picking up his first Top 10 victory over Tomas Berdych at the Miami Open.

For the next 14 years, he would not leave the elite ranking category—climbing as high as No. 3 in the world.

Come next Monday, that remarkable streak will end. With quarterfinal points to defend at the Rolex Monte-Carlo Masters, Dimitrov’s early 2026 struggles continued Tuesday in a 6-4, 2-6, 6-3 first-round defeat to Tomas Martin Etcheverry.

The Bulgarian dropped to 2-7 on the year, though his upcoming exit from the Top 100 is in part due to the time he missed last season. Dimitrov played just one test match at the Paris Rolex Masters following the pectoral muscle injury he sustained with a two-set lead on Jannik Sinner in the fourth round of Wimbledon. The impending drop comes before the Roland Garros cutoff is made, meaning Dimitrov will need a wild card

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Jannik Sinner reacts to "solid" opening win over Ugo Humbert | Monte Carlo Interview

Sinner, meanwhile, upped his unbeaten set streak in ATP Masters 1000 competition to 36 as he and defending champion Carlos Alcaraz both rolled through their openers. Coming off a successful Sunshine Double sweep at Indian Wells and Miami, the world No. 2 handily dispatched Ugo Humbert with a 6-3, 6-0 victory.

“I’m just very happy to be back in Europe, especially here at home sleeping in my own bed. You’re seeing tennis in a different view, you’re slightly more relaxed coming here knowing the place really well,” he told Tennis Channel’s Prakash Amritraj.

“It was a really solid performance today against a very tough player, lefty.”

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Sinner is bidding to lift his first clay-court crown since his July 2022 triumph over Alcaraz in Umag. He finished runner-up to the Spaniard in last year’s Rome and Roland Garros finals.

Alcaraz was equally comprehensive in kickstarting his bid to hold off Sinner from reclaiming the No. 1 ranking. The 22-year-old dismissed Sebastian Baez, 6-1, 6-3, breaking five times from 10 opportunities.

Hubert Hurkacz, Matteo Berrettini and Fabian Marozsan were among those to advance out of first-round action.