Novak Djokovic is all set to tune his game ahead of the US Open, but the Serb has gotten quite a tricky draw at the Cincinnati Open. Playing at the event after three years, the 24-time Major champion will look to get a few matches in, but the potential opposition might be a difficult obstacle for him.

Djokovic opens with a bye before facing the winner of Thiago Agustin Tirante and Jan Choinski, a manageable start on paper. The trouble begins in the third round, where Jack Draper or Matteo Arnaldi likely await, both players with recent wins over him. Arnaldi beat Djokovic in Madrid last year, and Draper got him at Indian Wells this year in an epic fourth-round battle that went to a third-set tiebreak.

It doesn’t get easier from there. A round of 16 meeting with either Jakub Mensik, who beat Djokovic in last year’s Miami Open final, or Luciano Darderi, fresh off a Montreal quarterfinal run, looms next. Should he get through that, Alex de Minaur is the projected quarterfinal opponent, and Alexander Zverev sits on the other side of a potential semifinal. Making matters tougher, Rafael Jodar, one of the hottest players on tour after reaching the Montreal semifinals, is also tucked into Djokovic’s half of the draw. It’s a path that offers Djokovic little room to ease back into competition, especially since he hasn’t played since losing to Jannik Sinner in the Wimbledon semifinals.

Taylor Fritz and Ben Shelton have drawn considerably friendlier roads by comparison, at least early on. Fritz’s section includes Zizou Bergs, Joao Fonseca, Casper Ruud, Daniil Medvedev, and Andrey Rublev. Ruud holds a 3-1 head-to-head edge over Fritz, but that lone Fritz win came on an outdoor hard court at the US Open, which should make him the favorite if the two meet again on Cincinnati’s hard courts. Fritz isn’t exactly cruising into the event either, though. He lost immediately in Montreal last week to Tirante, the same player who could open Djokovic’s tournament.

Shelton’s draw looks similarly gentle, with Jenson Brooksby, Ignacio Buse, Ugo Humbert, and Lorenzo Musetti in his section. Musetti holds the head-to-head edge, but Shelton won their most recent meeting, and given how both are playing right now, he’d likely be favored if that rematch happens.

For Djokovic, the difficulty of the draw doesn’t erase the opportunity sitting in front of him. With both Carlos Alcaraz and Jannik Sinner out of Cincinnati, this is as clean a shot as he’s had in years at a Masters title.

Novak Djokovic Has a Big Opportunity of Clinching a Masters Title After Three Years

With Alcaraz and Sinner rewriting the record books over the past few seasons, it’s been almost three years since Djokovic last won a Slam. His last Masters 1000 title came in that same 2023 season, when he won both Cincinnati and Paris. He still leads the sport in Masters wins overall, with 40 titles at that level.

Since the start of 2024, Djokovic has played 11 of the 24 Masters events held, prioritizing his health and freshness for the Slams over a full schedule. Even in that stretch, he still reached two Masters finals, losing to Sinner and Mensik respectively. Cincinnati marks his third Masters 1000 appearance of 2026, after Indian Wells and Rome.

Cincinnati wasn’t always kind to him. He lost five finals there, to players like Roger Federer and Andy Murray, before finally winning the title in 2018. He holds a 45-12 record at the event across his career, with his most recent title coming in 2023, when he beat Alcaraz in one of the best three-set finals of that season.

With Alcaraz and Sinner both absent this year, Djokovic’s path to a fourth Cincinnati title starts against the winner of Tirante and Choinski once the tournament gets underway this week, and a strong run here would send him into the US Open with real momentum behind him.