Novak Djokovic Breaks Wimbledon Win Record, Osaka Upsets Sabalenka to Reach Quarterfinals

The second week of Wimbledon 2026 began on Sunday with the round of 16 matches, highlighted by Novak Djokovic's historic victory and Naomi Osaka's upset over top seed Aryna Sabalenka. Djokovic advanced to the quarterfinals after a four-set win against qualifier Roman Safiullin, 6-7(6), 3-6, 6-3, 3-6. This marked Djokovic's 106th Wimbledon win, surpassing Roger Federer's record for the most victories in the tournament's history. It was also his ninth consecutive and 17th overall quarterfinal appearance at Wimbledon, and his 66th at any Grand Slam event.

Djokovic faced a tough challenge from Safiullin, who started strong and pushed Djokovic to a tiebreak in the first set. Despite some frustration and 37 unforced errors, Djokovic managed to close the match after three and a half hours. He praised Safiullin's performance, calling it a difficult win. Meanwhile, world number one Yannick Sinner is set to face Japanese qualifier Shintaro Mochizuki, who is having his best Grand Slam run at 23 years old and ranked 151.

In the women's draw, Naomi Osaka stunned top seed Aryna Sabalenka with a 2-6, 6-7(2) victory to reach her first Wimbledon quarterfinal. Osaka ended Sabalenka's streak of 21 consecutive Grand Slam tiebreak wins and achieved her best Wimbledon result after previously never winning against a top-20 player on grass. Jessica Pegula also advanced to the quarterfinals for the second time by defeating fellow American 18-year-old Ivana Jovic 6-4, 3-6, 1-6, improving her 2026 record against American opponents to 8-0.

A notable Czech derby saw Karolina Muchova defeat Barbora Krejcikova 5-7, 7-5, 3-6, matching her best Wimbledon performance. Muchova, the 2024 Wimbledon champion, is currently ranked 38th but has shown strong form this tournament. The quarterfinals promise exciting matchups as the tournament progresses.

The next rounds will feature Djokovic aiming to extend his Wimbledon dominance, Osaka seeking to continue her breakthrough, and other top players battling for a place in the semifinals.