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Jasmine Paolini blazed past American Emma Navarro 6-2 6-1 to become the first Italian woman to make the Wimbledon semifinals.
Taylor Fritz toppled Alexander Zverev with a 4-6 6-7(4) 6-4 7-6(3) 6-3 victory to reach the quarterfinals.
World number one Jannik Sinner quelled the challenge of big-serving 14th seed Ben Shelton with a 6-2 6-4 7-6(9) victory.
Second seed Sinner kept his hopes of taking Djokovic's top ranking alive with a battling 2-6 6-3 6-2 6-1 win over local favourite Corentin Moutet.
Andrey Rublev became the highest men's seed to crash out at Roland Garros.
Eighth seed Ruud held his nerve as five unforced errors from Djokovic allowed him to go 3-0 up in the decider and he calmly closed out the victory.
Sinner won 88 per cent of his first serve points and thumped 15 winners to capture the title in South Florida after finishing as the runner-up in 2021 and 2023.
Alcaraz came from behind to beat Jannik Sinner before Medvedev edged out American Tommy Paul 1-6, 7-6(3), 6-2 in the second semifinal.
Third seed Coco Gauff served up 17 double faults but still managed to beat China's Yuan Yue 6-4, 6-3 to reach the women's semifinals in the Californian desert for the first time.
The 22-year-old fourth seed is the first Italian to win the Melbourne Park title.