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Coming into Acapulco, Jacopo Berrettini had lost all eight sets he previously contested in ATP Tour qualifying matches. The 24-year-old required a wild card to gain entry into the qualies stage of the 500-level event and it looked like the Italian’s singles stint would be short lived Saturday when he dropped an opening set, 6-0, to the No. 3 seed, Geoffrey Blancaneaux.

By late Tuesday evening however, the world No. 842 found himself in the second round—of the main draw—at the Abierto Mexicano Telcel alongside big brother Matteo. Having qualified into his first tour-level main draw following a three-set win over Blancaneaux and convincing victory against countryman Luciano Darderi, Berrettini led Oscar Otte, 3-6, 7-6 (3), 2-1, when the German retired due to a left knee injury.

With a rankings difference of 764 places in his favor, Otte began like the experienced competitor by securing an early break and shaking off moments of resistance to build a one-set lead. But after Berrettini saved a break point to hold in the opening game of the second set, he inserted himself into the match with three straight games. Though the advantage didn’t hold up, he stayed with Otte to reach a tiebreak.

In his most recent singles appearance prior to Acapulco, J. Berrettini lost in the second round of the M25 event in Vila Real de Santo Antonio.

In his most recent singles appearance prior to Acapulco, J. Berrettini lost in the second round of the M25 event in Vila Real de Santo Antonio.

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During the crucial stage of the encounter, it was Berrettini who emerged as the steadier player. Otte double-faulted at 1-1 and handed his opponent a second mini break with an erratic forehand at 1-4. As the two went to change sides, the 29-year-old took a seat. A medical timeout immediately followed, as the trainer worked on Otte's left knee. He soon saw the scoreboard leveled when Berrettini drilled a forehand up the line to send the clash into a decider.

With the area of concern taped, Otte played on for three games. Resorting to drop shots and big cuts, a break at love saw him fall behind 2-1—and Otte then decided it was best not to continue further. He is now 0-4 against the Berrettini family.

For the younger Berrettini, it clinched a maiden ATP match win and first Top 100 victory. The success thus far is projected to see him return well inside the Top 500. Pulling an upset over No. 8 seed Alex de Minaur Wednesday would enable Berrettini to surpass his career-high ranking of No. 388.

As for his brother, Matteo also advanced through a match that ultimately wasn’t completed. The former Wimbledon finalist led Alex Molcan, 6-0, 1-0, when the Slovakian stopped due to a wrist injury.