Novak Djokovic appears to be facing a challenging road to Grand Slam title No. 24 at Wimbledon, which begins Monday at the All England Club.

While World No. 1 Carlos Alcaraz of Spain opens with France’s Jeremy Chardy, second-seeded Djokovic starts his quest for a record-tying eighth Wimbledon crown against Argentina’s Pedro Cachin.

Djokovic could see Stan Wawrinka in the third round and Australian Nick Kyrgios in the quarterfinals. The Serbian star defeated Kyrgios in the men’s final in 2022.

Djokovic, 36, has won his last 28 matches overall at Wimbledon and his last 39 on Centre Court.

Only one player in the men’s draw has defeated Djokovic on grass — wild-card Andy Murray. Murray drew Ryan Peniston in the All-Britain opener with the prospect of seeing No. 5 seed Stefanos Tsitsipas of Greece in the second round. Tsitsipas plays Dominic Thiem (Austria), whose Slam history includes dealing Djokovic a loss at Roland Garros (2017) and the nearly five-hour classic with Spain’s Rafael Nadal in the 2018 U.S. Open quarterfinals.

No. 4 seed Casper Ruud of Norway drew an opener against French qualifier Laurent Lokoli, who is ranked just inside the top 200.

No. 3 seed Daniil Medvedev of Russia resides in a quarterfinal bracket with No. 32 Ben Shelton, the 20-year-old American who reached the Australian Open quarterfinals earlier this year. In the same pod is Great Britain’s Cameron Norrie, who reached the Wimbledon semifinals in 2022, and No. 16 seed Tommy Paul, another American who reached the Australian Open semifinals year.

Alcaraz could reach the semifinals playing only one match against a top-9 seed — Denmark’s Holger Rune is sixth — in a quarterfinal grouping that includes 2021 runner-up Matteo Berrettini of Italy and No. 10 seed Frances Tiafoe. The 25-year-old Tiafoe, who enters with a grass court title at Stuttgart (Germany), reached the fourth round at Wimbledon in 2022.

–Field Level Media