Seven Grand Slam titles at Wimbledon. Twenty-four in total. A record-extending 25th is within reach, and a draw that has ensured he will have to earn every last one of them. Novak Djokovic is the seventh seed at the All England Club and has played just a small fraction of what his rivals have played this season, while the path ahead gets tougher by the round. In the end, if all goes as planned, Jannik Sinner is in the semi-finals. The defending champion. The man he beat at the semifinals of the Australian Open. The one obstacle he has never been able to clear at Wimbledon. 

The draw begins straightforwardly enough. Djokovic faces Wu Yibing in the first round, a Chinese contender who is only just inside the top 100 and has very little grass-court experience and no previous record against the Serb. Djokovic’s career grass-court record is 125 wins and 21 defeats, representing an 85.6 percent win rate, a mark that illustrates the extent to which he has conquered a hard-to-master surface for which other players struggle for years. Wu is unlikely to change that number. 

The second round is where it gets more challenging. Djokovic is projected to face either Stefanos Tsitsipas or Hugo Gaston. The likely fixture would be against the Greek player, as he has more experience and already has won a game against Gaston. Tsitsipas and Djokovic have met 14 times in their career, with the Serbian leading the head-to-head 12-2. 

Most importantly, they haven’t played on grass before, the one factor that makes this round no formality. Tsitsipas, who has a career grass record of 23 wins and 19 losses, has been plagued by his limitations with baseline approaches on grass, and Djokovic’s serve and return on grass is one of the most suffocating in the history of the tournament.

The third round presents Arthur Rinderknech, who enters Wimbledon seeded 25th. The Frenchman is a capable big server who can cause problems for players who are not fully switched on. However, Novak Djokovic has faced much tougher challenges at this stage of a Grand Slam, and there’s no head-to-head record to indicate anything more than a routine test. 

The draw gets much tighter in the fourth round. Djokovic is seeded to face either Andrey Rublev or Joao Fonseca. Rublev has proved to be a menace on grass in recent years, his best result coming in 2023 when he made it to the Wimbledon quarter-finals before falling to Djokovic in a four-set match, a result that reflects their overall standing: Djokovic leads 5-1 across their six meetings. Fonseca is the name that carries the bigger storyline. It was the 19-year-old Brazilian who beat Djokovic at the third round of the Roland Garros in five sets. This fourth-round match-up at Wimbledon would be one of the most interesting matches on both sides of the draw. 

The quarter-final is where the draw makes its most pointed statement. It’s a big matchup with third seed Felix Auger-Aliassime waiting in the last eight. They have met twice. Their meeting was in Rome in 2022 on clay, with Djokovic winning 7-5, 7-6. The second meeting came later in the year at the Laver Cup, where the Canadian beat the Serb 6-3, 7-6. But Auger-Aliassime is a different player in 2026. He has won 52 of 74 matches in all conditions (60 percent on grass in the last 52 weeks) and is averaging 10.2 aces per game, while his career average is 8.7. He has the ability and the serve to test Djokovic when five rounds of fatigue will matter for a 39-year old who has rarely competed this season. 

Sinner looms large in the semi-finals

The semi-final projection is the one that will be remembered for the draw. Novak Djokovic against Jannik Sinner, the defending champion and world No. 1, on the surface where Sinner claimed his first Wimbledon title last year. In 2025, Sinner beat the Serbian in the Wimbledon semi-finals in straight sets before going on to lift the trophy. It was the other way around at the Australian Open in January. Djokovic rallied from a two-set down to overcome the Italian 3-6, 6-3, 4-6, 6-4, 6-4 in four hours and nine minutes, breaking a five-match losing streak that could have spelled the end of the final years of his career. 

The overall head-to-head now stands at Sinner leading 6-5, with Djokovic having won their first three meetings before Sinner ran off five consecutive wins before the Melbourne reversal.

After losing in the second round of the French Open, the Italian has not played any matches. The same goes for Djokovic. The Serbian was supposed to play an exhibition match at the Giorgio Armani Classic in London, but withdrew without explanation. However, he was seen training on the Wimbledon grounds on Thursday, including a session alongside Sinner himself. 

A final, if it arrives, would most likely bring Djokovic against second seed Alexander Zverev. Djokovic leads that head-to-head 9-5, though the gap has closed in recent years. Zverev enters Wimbledon having won his first Grand Slam title at Roland Garros, and now the question is, can the grass be the next big surface he conquers? 

The condition on which everything rests is not the draw but the body. Djokovic has not played a competitive match since losing to Fonseca in the third round at Roland Garros on 29 May, a span of a month going into Wimbledon without match action. In recent times, he’s always come into Grand Slams under-prepared, by conventional standards. Last year, he made the semi-finals without playing a single grass-court game at Wimbledon, and he did the same before the US Open.

The exhibition withdrawal this week is no different from other load management withdrawals that have happened in the past. However, the question of fitness will not be resolved until he eventually arrives on Center Court on Monday. Seven Wimbledon titles give him a blueprint no other player in the draw possesses. Many believe that if he wants to extend his tally of 24 Grand Slams, grass is his best chance as the surface rewards experience. Whether the body can sustain across a fortnight shaped like this one is the question his entire season has been building towards.