Apr 26, 2025, 11:41 AM ET

MADRID — Novak Djokovic lost to Matteo Arnaldi in the opening round of the Madrid Open on Saturday, extending the 24-time Grand Slam winner’s struggles on clay ahead of Roland Garros.

Arnaldi won 6-3, 6-4, delaying Djokovic’s search for a career 100th title.

Djokovic also lost his opener to Alejandro Tabilo at the Monte Carlo Masters two weeks ago.

It was the first meeting between Djokovic and 44th-ranked Arnaldi of Italy.

Russian teenager Mirra Andreeva reached the last 16 for the third straight year by defeating Magdalena Frech 7-5, 6-3.

Andreeva, ranked No. 7, has yet to lose before the Madrid fourth round.

She reached that stage for the first time in 2023 while playing as a wild card in her second WTA main draw. Last year, her first big quarterfinals came in the Spanish capital.

“I was very, very nervous,” Andreeva said. “I still struggle to find my best tennis in Madrid. Super happy that I could manage to play consistent throughout the whole match.”

Andreeva, who will turn 18 on Tuesday, will next face Ukrainian qualifier Yuliia Starodubtseva, who defeated 18th-seeded Liudmila Samsonova in three sets.