Italy will have three players in the Wimbledon quarterfinals after Flavio Cobolli and Jasmine Paolini won their fourth-round matches on Monday, joining Jannik Sinner in the last eight.
Cobolli beat Australian fifth seed Alex de Minaur 7-5, 7-6(4), 6-3 on No. 1 Court, then Paolini ended Alexandra Eala’s run 6-4, 4-6, 6-3 on Centre Court. Sinner had already reached the quarterfinals on Sunday. The three advances arrive weeks after Italy sent three men into the Roland Garros quarterfinals, a run of collective depth that no longer reads as coincidence.
Cobolli. The 24-year-old’s win was the sharper statement. It was the first meeting of two top-10 men at this year’s Championships, and Cobolli took it by recovering from 2-5 down in the second set and a break down in the third, closing on his first match point with a 135 mph serve down the T that de Minaur could barely touch. Reaching the last eight for the second straight year made him the third Italian man, after Nicola Pietrangeli and Sinner, to reach multiple Wimbledon quarterfinals.
It also continued a breakthrough season that has carried him from a first-round loss at the Australian Open to the Roland Garros final last month, where he fell to Alexander Zverev. The world No. 10 will next play Arthur Fery, the British wild card who eliminated Grigor Dimitrov earlier Monday.
Paolini. Paolini’s route was more about survival than sharpness. The 13th seed, whose season has been disrupted by a foot injury that left her one grass-court match before the tournament, dropped the second set to Eala before breaking to serve out the third. It returned her to a Grand Slam quarterfinal for the first time since 2024, when she reached the finals at both Roland Garros and Wimbledon. Roger Federer watched from the Royal Box alongside Formula One championship leader Kimi Antonelli; Paolini, who called Federer her idol, said afterward she had spent the match telling herself to stay focused. She next faces Marta Kostyuk.
The pipeline. The through-line is not any single result but the depth behind them. Sinner, the world No. 1 and defending champion, meets Jan-Lennard Struff on Tuesday. Cobolli, a top-10 player and major finalist, meets Fery. Paolini, a two-time major finalist, meets Kostyuk. A decade ago Italy rarely carried a single contender into a Slam’s second week; it now arrives with several across both draws, the product of a development system that has moved from producing occasional talents to sustaining a generation of them. The Roland Garros quarterfinal trio in June and the Wimbledon three in July are the same story told twice in a month.
Whether any of them reaches a semifinal is a separate question. Sinner is favored against Struff; Cobolli faces a home crowd firmly behind Fery; Paolini meets a Kostyuk playing the best grass tennis of her career. But the count itself — three of the last eight, on a surface where Italian success has historically been scarce — is the result that frames the fortnight.
