Novak Djokovic cracked a wry smile as he was updated on a Wimbledon fan who produced an iconic gesture during his 2019 showdown with Roger Federer while rooting against the Serbian great

The 38-year-old overcame a first-set loss to take a 6-7, 6-2, 7-5, 6-4 victory over Italian Flavio Cobolli to advance to the semifinals for the 14th time at the All England Lawn Tennis & Croquet Club. Djokovic has now reached the final four at Wimbledon more than any other men's tennis player, surpassing Roger Federer on Wednesday.

Novak Djokovic's pursuit of yet more career milestones continued unabated as he reached a record 14th Wimbledon semi-final and a showdown with world number one Jannik Sinner on Wednesday. The 38-year-old Serb recovered from a set down to beat Flavio Cobolli 6-7(6) 6-2 7-5 6-4 and is now only two victories away from an unprecedented 25th Grand Slam title.

Novak Djokovic smiled after learning a fan who opposed him with an infamous gesture during his 2019 Wimbledon final with Roger Federer has changed her tune.

Novak Djokovic is still in the hunt for his 25th career Major title when he takes on No. 22 seed Italian Flavio Cobolli for a spot in the semifinals.

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

It's a day off the for the men, who play their semi-finals tomorrow. Injury doubts cloud over Novak Djokovic 's clash with Jannik Sinner. The duo are both carrying fitness issues. Carlos Alcaraz will hope to continue his surgent form against the impressive Taylor Fritz.