Novak Djokovic's quest for a record-extending 25th Grand Slam title at Wimbledon in 2025 has run into a familiar and formidable opponent: Jannik Sinner. The world No. 1 stands between the Serbian legend and another Wimbledon final, a stage Djokovic has graced in each of the past six championships. This semi-final clash is a rematch of their 2023 encounter at the same stage, where Djokovic emerged victorious. However, much has changed since then, and Sinner now holds a 5-4 lead in their head-to-head record, including a recent victory at the Roland Garros semi-finals.

Djokovic's path to the semi-finals has been anything but smooth. In his quarter-final match against Flavio Cobolli, the 38-year-old battled back from a set down to win 6-7(6), 6-2, 7-5, 6-4. The match was not without its drama, as Djokovic suffered a "nasty fall" while holding match point. Despite the slip, he managed to finish the match, though he admitted to some uncertainty about the lasting impact of the fall. "It was a nasty slip but that is what happens when you play on the grass," Djokovic said. "I think I hadn't fallen so far this year... It did come at an awkward moment but I managed to find a good serve and close it out. I am going to visit this subject now with my physio".

Prior to the Cobolli match, Djokovic also dropped the first set against Alex de Minaur in the fourth round. Despite the slow starts, Djokovic has shown resilience and experience, overcoming these hurdles to reach a record-breaking 14th Wimbledon semi-final. This achievement surpasses Roger Federer's previous record of 13 semi-final appearances at Wimbledon. It also marks Djokovic's 52nd Grand Slam semi-final, tying him with Chris Evert for the most in the Open Era.

Djokovic acknowledged the challenges posed by the younger generation of players, including Cobolli and, of course, Sinner. "Another thing that makes me feel very young is competing with youngsters," Djokovic said. "[Cobolli] is definitely one of the guys that we'll be seeing in the future much more so I wish him all the best... speaking of the young guys I'm going to have Sinner in the next round so I look forward to that that's going to be a great matchup".

Sinner, on the other hand, has had a relatively comfortable run to the semi-finals, allaying concerns about an elbow injury. He defeated Ben Shelton in straight sets in the quarter-finals. Sinner is aware of the challenge that Djokovic poses, especially at Wimbledon, where the Serbian has dominated for years.

Djokovic's form has been a topic of discussion throughout 2025. While he reached the semi-finals of the Australian Open, an injury forced him to retire. Since then, he has experienced some early exits in tournaments, though he did reach the final of the Miami Open. Despite the recent struggles, Djokovic remains a formidable opponent, especially on grass. His serve and return game are well-suited to the surface, and his experience at Wimbledon is unmatched.

The upcoming semi-final clash between Djokovic and Sinner is highly anticipated. Sinner's recent form and head-to-head advantage make him a dangerous opponent, but Djokovic's experience and determination cannot be discounted. The match promises to be a thrilling encounter between the established champion and the rising star, with a place in the Wimbledon final and a shot at Grand Slam glory on the line.