Novak Djokovic and Jannik Sinner will be squaring off for the 12th time in their careers when they battle in a blockbuster semifinal at Wimbledon on Friday afternoon.
Sinner leads the head-to-head series 6-5. After losing four of their first five meetings, the Italian won five in a row — including in the semifinals of three different majors (2024 U.S. Open, 2025 French Open, and 2025 Wimbledon). Djokovic, though, finally turned the tide back in his favor by scoring a 3-6, 6-3, 4-6, 6-4, 6-4 upset in Australian Open semifinals at the start of 2026.
The 24-time Grand Slam champion gets another shot at Sinner on the heels of a thrilling quarterfinal against Felix Auger-Aliassime, which he survived 7-6(10), 3-6, 6-3, 6-7(4), 7-6(10-4) after five hours and 15 minutes. It was the longest QF match in Wimbledon history and Djokovic’s longest match ever in SW19. It has been a relatively difficult fortnight the whole way for the 39-year-old, who needed four sets to get past Yibing Wu, Arthur Rinderknech, and Roman Safiullin.
Sinner has also been tested. The world No. 1 played a five-setter against Miomir Kecmanovic in the opening round and has since been pushed to four tiebreakers — two against Nuno Borges in the last 64. Sinner’s contest against Jan-Lennard Struff on Tuesday was straight sets, but the 7-5, 7-6(4), 6-3 scoreline was anything but routine.
Although Sinner certainly hasn’t been at his best this fortnight, he has been producing the goods when it matters most. That is encouraging — and so is the fact that the 24-year-old played for two hours and 35 minutes on Tuesday — two hours and 40 minutes less than Djokovic. Fortunately for the underdog, he has two days off.
To be abundantly clear, it will not come as a huge surprise if Djokovic wins. He really shouldn’t be as big of an underdog as the odds are indicating — not in a Grand Slam, where he almost always seems to be at or near his best. Still, it’s tough to pick against Sinner when he is 100 percent physically — which looks like the case at the All-England Club, and much unlike what happened at Roland Garros.
Pick: Sinner in 4
Ricky contributes to 10sballs.com and also maintains his own tennis website, The Grandstand. You can follow him on Twitter at @Dimonator.