Flavio Cobolli and Jasmine Paolini swept into the Wimbledon quarter-finals on Monday, delivering a double success for Italian tennis on the second Monday of the Championships. Cobolli, the world No.10, dismissed fifth-seeded Australian Alex de Minaur 7-5, 7-6(4), 6-3 on Court One, while Paolini, a finalist here in 2024, overcame Filipina Alexandra Eala 6-4, 4-6, 6-3 on Centre Court. Both victories came in straight sets, though each required resilience: Cobolli rallied from 2-5 down in the second set before dominating the tiebreak, and Paolini held off a spirited challenge from Eala, who had eliminated defending champion Iga Swiatek in the previous round.

For Cobolli, it marks a second consecutive quarter-final at the All England Club, a feat matched among Italian men only by Jannik Sinner and Nicola Pietrangeli. He will next face the winner of the all-wildcard clash between Britain’s Arthur Fery and Bulgaria’s Grigor Dimitrov. Paolini, who has struggled for form in 2026, described the year as 'hard' but said she felt she was 'on the right path.' She will meet Ukraine’s Marta Kostyuk for a place in the semi-finals.

The day’s other major storyline unfolded earlier, when Japan’s Naomi Osaka eliminated world No.1 Aryna Sabalenka 6-2, 7-6(4). The result, viewed from Tokyo as confirmation of Osaka’s return to the elite, sent the four-time major champion into her first Wimbledon quarter-final since 2021. Sabalenka, who also fell in the Roland Garros quarter-finals, has now failed to reach the last four in consecutive Grand Slams, a dip in form that has drawn scrutiny in European tennis circles.

British attention remained fixed on Fery, the 23-year-old wildcard who became the first home player to reach the men’s fourth round since 1993. His match against Dimitrov, a former world No.3 also on a wildcard, was scheduled second on Centre Court and represented the first all-wildcard fourth-round meeting at Wimbledon in the Open era. Meanwhile, the men’s draw guarantees a first-time finalist, with Taylor Fritz, Alexander Zverev and others still in contention.

With Sinner already through to the last eight, Italy has three quarter-finalists across the singles draws for the first time at Wimbledon. Cobolli and Paolini will resume their campaigns on Wednesday, while Fery carries home hopes into the evening session.