The second round of Wimbledon 2026 saw four Italian players advance to the third round. Matteo Berrettini defeated Frenchman Arthur Fils, seeded 20th, in four sets with a score of 6-4 7-5 3-6 6-3. Berrettini, currently ranked 51st in the world, reached the third round at Wimbledon for the fourth time in his career, confirming his familiarity with grass courts. The 30-year-old had been limited by physical problems over the previous two and a half years. Flavio Cobolli overcame Australian James Duckworth in four sets. Lorenzo Sonego prevailed over Canadian Gabriel Diallo in a five-set match lasting over four hours, with a final score of 7-6 4-6 7-6 6-7 6-2. In the women's draw, Jasmine Paolini defeated Swiss Viktorija Golubic in two sets, 7-6 6-4. Tyra Grant was instead eliminated in two sets by Czech Marie Bouzkova.

In the third round, world number one Jannik Sinner defeated American Jenson Brooksby, ranked 81st, in three sets: 6-4 6-3 6-4, in two hours and 13 minutes. The match was more competitive than the scoreline might suggest. Brooksby created three break opportunities in the second set but failed to convert them. In the third set, Brooksby broke Sinner's serve first, but the Italian immediately broke back and then secured a decisive break at 5-4, closing the match on his third match point. After the match, Sinner said he was satisfied with the victory and felt he had made small improvements, though he acknowledged he needed to manage certain situations better. At one key moment in the third set, Sinner gestured to the crowd by putting a finger to his ear to request their support, an unusual gesture for him.

Sinner's next opponent will be Japan's Shintaro Mochizuki, ranked 151st, who came through the qualifiers and reached the round of 16 by defeating Spanish prospect Rafael Jodar in four sets. The only previous meeting between Sinner and Brooksby dated back to 2021 in Washington, where Sinner won in two sets. Brooksby's career has been marked by challenges: he has dealt with a severe form of autism since childhood and was suspended for 13 months for missing three anti-doping tests, a situation tied to his difficulty concentrating on multiple tasks at once.

In the other third-round matches involving Italians, Flavio Cobolli advanced to the round of 16 after a five-set battle against Russia's Karen Khachanov, winning 0-6 7-6 6-7 6-2 6-2 in a match lasting about four hours. Jasmine Paolini dominated Greece's Maria Sakkari 6-1 6-2 and will face Filipino Alex Eala in the next round. Matteo Berrettini's run ended in a five-set defeat to Bulgaria's Grigor Dimitrov, 6-3 6-4 3-6 5-7 6-3, despite having come back from two sets down. Lorenzo Sonego was eliminated by American Taylor Fritz, seeded 7th, in four sets: 4-6 6-3 6-4 7-6. The doubles team of Simone Bolelli and Andrea Vavassori also continued their tournament run.

After the third round, three Italian players remained in the singles draws: Jannik Sinner and Flavio Cobolli in the men's tournament and Jasmine Paolini in the women's.