Novak Djokovic starts his offer for a fifth Shanghai title when he met fellow veteran Marin Cilic during the second round on Friday. Tallon Griekspoor starts his fourteen days against an in-form Jenson Brooksby.
Marin Cilic vs. (4) Novak Djokovic
Cilic and Djokovic will give up in their career for the 22nd time when they collide in round two of the Rolex Shanghai Masters on Friday. Djokovic dominates the head-to-head series 19-2, with Cilic’s some wins on the inner hard courts of the Paris Masters in 2016 and on the grass of Queen’s Club in 2018. They have not confronted each other since 2022, when Djokovic 6-3, 6-4 in the Tel Aviv-final.
Both players are clearly at the twilight of their career. Djokovic, 38, sparingly plays outside the Grand Slams where he reached four semi-finals in 2025. Cilic, 37, has missed some time in recent seasons due to physical problems, but is back in the top 100 at number 94 in the world in the world in the world in Wimbledon. The only way Djokovic would lose this match is if he is not motivated, but the fifth arranged Serbian has no reason to play this event if that was not the case. Count on Djokovic Cruising in straight sets.
Pick: Djokovic in 2
(27) Tallon Griekspoor vs. (PR) Jenson Brooksby
Griekspoor and Brooksby go for the second time in their career and for the second time this year. Their only earlier meeting came in Wimbledon, where Brooksby 6-2, 7-5, 6-3 rolled. The 24-year-old American is currently in excellent form, and his Asian swing already includes a semi-final in Tokyo (Beat Holger Rune in the Quarters, lost from Taylor Fritz). Brooksby immediately came back in gear to beat the James Trotter qualifying 7-6 (2), 6-1 in the Shanghai opening round.
Griekspoor has cooled since a hot start of the season. The 31st ranking list Dutchman is at a loss of seven games that will return to the Post-Wimbledon Clay-Court Swing in July. He has not reported anyone in the top 100 since he recorded the Mallorca title in June. With the extra advantage that he already has a competition under his belt in Shanghai, Brooksby has every reason to extend the misery of Greek track.
Pick: Brooksby in 2
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