Novak Djokovic will begin his bid for a fifth Shanghai title when he meets fellow veteran Marin Cilic during second-round action on Friday. Tallon Griekspoor is kicking off his fortnight against an in-form Jenson Brooksby.
Marin Cilic vs. (4) Novak Djokovic
Cilic and Djokovic will be squaring off for the 22nd time in their careers when they clash in round two of the Rolex Shanghai Masters on Friday. Djokovic is dominating the head-to-head series 19-2, with Cilic’s only wins coming on the indoor hard courts of the Paris Masters in 2016 and on the grass of Queen’s Club in 2018. They have not faced each other since 2022, when Djokovic triumphed 6-3, 6-4 in the Tel Aviv final.
Both players are obviously in the twilight of their careers. Djokovic, 38, plays sparingly outside of the Grand Slams–at which he reached four semifinals in 2025. Cilic, 37, has missed a bunch of time in recent seasons due to physical problems but is back inside the top 100 at No. 94 in the world thanks in part to a fourth-round run at Wimbledon. The only way Djokovic would lose this match is if he isn’t motivated–but the fifth-ranked Serb has no reason to play this event if that wasn’t the case. Count on Djokovic cruising in straight sets.
Pick: Djokovic in 2
(27) Tallon Griekspoor vs. (PR) Jenson Brooksby
Griekspoor and Brooksby will be going head-to-head for the second time in their careers and for the second time this year. Their only previous encounter came at Wimbledon, where Brooksby rolled 6-2, 7-5, 6-3. The 24-year-old American is in outstanding form right now, and his Asian swing already includes a semifinal showing in Tokyo (beat Holger Rune in the quarters, lost to Taylor Fritz). Brooksby got right back in gear to beat qualifier James Trotter 7-6(2), 6-1 in the Shanghai opening round.
Griekspoor has cooled off since a hot start to the season. The 31st-ranked Dutchman is on a seven-match losing streak dating back to the post-Wimbledon clay-court swing in July. He has not defeated anyone in the top 100 since capturing the Mallorca title in June. With the extra advantage of already having a match under his belt in Shanghai, Brooksby has every reason to extend Griekspoor’s woes.
Pick: Brooksby in 2
WWW?
Cilic had been on a 6 match skid, even losing to lowly Basavareddy who couldn’t even get past R1 of qualies here or in Beijing, until he finally just got a win, but yeah it doesn’t look good for him, Nole 6-3, 6-2.
Well yeah Brooksby is playing alright, but he’s probably tired by now with all the recent match play and travel and Griekspoor is going to break the streak sometime, so why not now where he can take advantage of a tired Brooksby, Griekspoor 2-6, 7-5, 6-3.
Djokovic in 2, Brooksby in 2
Results are Nole 7-6(2), 6-4 and Griekspoor with a crazy scoreline, 6-1, 1-6, 6-1.