Croatian qualifier Dino Prižmić produced a major upset at the Madrid Open on Friday, defeating world number six Ben Shelton in a dramatic second-round clash.

The 20-year-old, ranked 87th in the world, claimed a 6-4, 6-7(4), 7-6(5) victory after a three-hour battle to record the biggest win of his career and his first against a top-10 opponent.

Shelton, who had lifted the Munich Open title just days earlier, struggled to make an impact on return and was unable to earn a single break point against Prižmić’s serve.

The defeat marks an early exit for the American star in Madrid, while Prižmić moves forward after a breakthrough performance on the clay courts in Spain.

Italian Lorenzo Musetti, ranked world number nine, progressed at the Madrid Open with a straight-sets victory over Hubert Hurkacz, winning 6-4, 7-6(4).

He was later joined in action by compatriot Jannik Sinner, the world number one, who was scheduled to face France’s Benjamin Bonzi.

In the women’s draw, world number two Elena Rybakina battled through a tough contest to reach the third round, edging past Elena-Gabriela Ruse 4-6, 6-3, 7-5.

Rybakina, who claimed the Australian Open title in January and won in Stuttgart last week, struggled early in the match, committing 24 unforced errors compared to just eight winners in the opening set before recovering to secure the win.

Elena Rybakina battled through a demanding contest at the Madrid Open, eventually completing a hard-fought comeback to reach the third round after defeating Elena-Gabriela Ruse 4-6, 6-3, 7-5.

After edging a tense second set, Rybakina recovered from a break down in the decider and sealed victory on her third match point, underlining her resilience in difficult conditions.

The world number two will next face Zheng Qinwen, who also progressed after a tough win over Sofia Kenin.

Speaking after the match, Rybakina admitted she “basically survived” the encounter and acknowledged it was far from her best performance. She praised Ruse’s aggressive, deep hitting, which made the match especially challenging.

The Kazakhstani star also highlighted issues with her serve but expressed relief at getting through, adding that she hopes to produce a stronger performance in the next round.