He passed Roger Federer, who has made the final four of Wimbledon 13 times. Jimmy Connors has 11 appearances followed by Boris Becker with 9. It's another key record that adds to Djokovic's case as the best player to ever grace Wimbledon Centre Court.

Novak Djokovic has reached the Wimbledon semifinals for a men’s-record 14th time as he pursues his unprecedented 25th title from all Grand Slam tournaments.

Novak Djokovic defeated Flavio Cobolli 6-7 (6), 6-2, 7-5, 6-4 on Wednesday to reach his 14th Wimbledon semifinal, breaking a tie with Roger Federer for the most among men in tournament history.

For the 14th time in his career, Novak Djokovic will stride out onto Centre Court for a Wimbledon semi-final. The 38-year-old will face world number one Jannik Sinner on Friday for a place in the final, a stage he has not failed to reach at SW17 since 2017.

A regular at tennis tournaments, Jelena Djokovic opted for summertime knits with her attire. On Monday, Djokovic styled a blue and white cable-knit vest courtesy of contemporary British fashion brand Varley. She wore the garment overtop a long-sleeve white shirt. Djokovic coordinated the vest with a pair of gray-blue cargo pants.

Djokovic, who is looking for a record-equaling eighth Wimbledon title and a record-breaking 25th Grand Slam title, battled and then surged past the Italian No. 22 seed Cobolli 6-7 (6), 6-2, 7-5, 6-4 to set up Friday’s date with Sinner.

SportsLine tennis expert Jose Onorato reveals his 2025 Wimbledon picks for Wednesday's men's singles quarterfinal between Novak Djokovic and Flavio Cobolli

If ever there was a time for Novak Djokovic to shake off his troubles and share a dance with his son and daughter, it was after being tested to his limit against Alex de Minaur in the fourth round of Wimbledon on Monday.

Djokovic’s bid for an eighth Wimbledon title and 25th Grand Slam singles trophy overall will continue against No. 22 Flavio Cobolli of Italy. Cobolli reached his first major quarterfinal with a 6-4, 6-4, 6-7 (4), 7-6 (3) victory over 2014 U.S. Open champion and two-time major runner-up Marin Cilic.