Novak Djokovic takes another step toward multiple Wimbledon and Grand Slam milestones on Friday when he meets Arthur Rinderknech in the third round, one of three standout matches highlighted on the fifth day of the tournament. Defending champion Jannik Sinner is also in action in the last 32, while women’s world number one Aryna Sabalenka faces former French Open winner Jelena Ostapenko in a marquee clash.
Djokovic arrives in the last 32 after what was described as a “vintage” performance in his second-round win over Stefanos Tsitsipas on Wednesday, a straight-sets victory on Centre Court that underlined his push for an elusive 25th Grand Slam title. With records and history in view, the Serb’s next assignment comes against a seeded opponent he has never faced before.
Djokovic vs Rinderknech: records in reach in a first meeting
Djokovic (SRB x7) meets France’s Arthur Rinderknech (FRA x25) for the first time, with the seven-time Wimbledon champion carrying momentum from his emphatic second-round display. The 39-year-old’s performance against Tsitsipas was framed as a statement of intent to his title rivals, and his mood was buoyant enough that he even found time to prank a ball-girl during the match before jokingly challenging golf star Rory McIlroy, who was watching from the royal box, to a tennis match.
Beyond the lighter moments, the stakes are significant. Djokovic is one match win away from equalling Roger Federer’s Wimbledon men’s singles record of 105 match wins. He is also chasing Federer’s men’s record of eight Wimbledon titles, a target that would carry wider historical weight: it would break his tie with Margaret Court for the most Grand Slam crowns by either a man or woman, according to the preview.
There is another layer to the narrative as well. Winning Wimbledon would make Djokovic the oldest man to lift a Grand Slam trophy in the Open era. After beating Tsitsipas, Djokovic summed up his outlook with a simple line: “age is just a number”.
Rinderknech, the 25th seed, represents a new challenge in what has been a long Wimbledon career for Djokovic. With it being their first meeting, the third-round tie is framed as the next checkpoint in Djokovic’s pursuit of history rather than a rematch shaped by past encounters.
Sabalenka vs Ostapenko: a dangerous test for the women’s No. 1
On the women’s side, Aryna Sabalenka (BLR x1) faces Jelena Ostapenko (LAT) in what is billed as one of the ties of the round. Sabalenka leads their head-to-head 3-1, but the matchup comes with clear danger given Ostapenko’s pedigree and the stage of the tournament.
Sabalenka is bidding to win Wimbledon for the first time. Despite being a four-time Grand Slam champion and reaching 14 successive major quarter-finals, the preview notes she has not been at her “over-powering best” so far at the All England Club. The 28-year-old has never won Wimbledon and has lost in the semi-finals on each of her past three visits.
There is also a broader form line attached to her status as a consistent late-stage presence at majors: she has won only one of the last six Grand Slam tournaments. That context makes Ostapenko, the 2017 French Open champion, an “intriguing obstacle” for Sabalenka to clear.
Ostapenko, 29, reached the Wimbledon semi-finals eight years ago and is described as capable of rattling Sabalenka with her booming ground-strokes. Off court, Sabalenka has also been in the news for pleading with Wimbledon chiefs to let her dog Ash into the grounds of the All England Club, a request that has so far been rejected. The preview adds that a title run ending on July 11 might help her case.
Sinner vs Brooksby: defending champion seeks sharper rhythm
Defending champion Jannik Sinner (ITA x1) continues his campaign in the third round against American world number 81 Jenson Brooksby (USA). Sinner leads their head-to-head 1-0, and he enters the match still searching for the level that took him to the title last year.
Sinner ended Carlos Alcaraz’s two-year reign as Wimbledon champion with a “brilliant” final victory over the Spaniard in 2025, but the preview suggests he is “still some way from those lofty heights” heading into this last-32 meeting. It also notes that, for the first time in his career, Sinner opted not to play a Wimbledon warm-up event, and he looked “a little underprepared” in his first two wins over Miomir Kecmanovic and Nuno Borges.
There are additional questions around his 2026 form at the majors. The world number one has not reached a Grand Slam final this year and suffered a shock French Open second-round defeat in June after blowing a two-set lead against Juan Manuel Cerundolo.
Why Friday matters: history, pressure and a path forward
With Djokovic chasing match-win and title records, Sabalenka trying to turn repeated semi-final heartbreak into a first Wimbledon crown, and Sinner aiming to sharpen his level as the defending champion, the fifth day’s featured ties carry weight beyond a place in the fourth round. Each match offers a different kind of test: a first-time opponent for Djokovic with history on the line, a proven disruptor across the net for Sabalenka, and a form check for Sinner as he tries to build momentum deeper into the tournament.
