Djokovic’s Path to Calendar-year Grand Slam at U.S. Open is Laced With Familiar Foes

By Ricky Dimon

Novak Djokovic may see some recognizable faces on the other side of the net when he tries to secure the calendar-year Grand Slam this coming fortnight at the U.S. Open.

After Djokovic presumably makes quick work over teenager Holger Rune in the opening round, the world No. 1 will likely run into Jan-Lennard Struff immediately thereafter. He is sweeping that head-to-head series against Struff 5-0–including 3-0 in majors and 15-1 in total sets. Kei Nishikori, who is 2-17 lifetime against the Serb, could be up next. In the fourth round Djokovic has a chance of playing Taylor Fritz, whom the top seed overcame in a memorable five-setter at this year’s Australian Open.

Moving into the business end of the tournament, Djokovic is in the same quarter of the bracket as Matteo Berrettini. If that potential quarterfinal contest comes to fruition, it would be a rematch of the Wimbledon final–won by the 34-year-old in four sets. Djokovic is on a collision course for the semis with either Alexander Zverev, Denis Shapovalov, or Pablo Carreno Busta. The 20-time major champion lost to both Zverev and Carreno Busta at the Tokyo Olympics after beating Shapovalov in the Wimbledon semis.

Interestingly, Carreno Busta went up against Djokovic, Shapovalov, and Zverev last year in New York. The Spaniard was the beneficiary of the default heard ’round the world, outlasted Shapovalov in five sets in his next match, and then fell to Zverev from two sets up with a spot in his first slam final on the line.

Jannik Sinner and Gael Monfils could also be factors in the Zverev-Shapovalov-Carreno Busta section of the draw.

In the other half, the projected semifinal is Daniil Medvedev vs. Stefanos Tsitsipas. When the Big 3 are gone, this has the makings of becoming the best rivalry in men’s tennis. Medvedev has won six of their eight encounters, but Tsitsipas has taken two of the last three.

Of course, there is a long way to go before those two competitors can be thinking about the final weekend. Tsitsipas won’t be looking past his first-round test, because that will come against none other than 2012 U.S. Open champion Andy Murray. The third-ranked Greek could eventually oppose Ugo Humbert in round four and Andrey Rublev in the quarters. Humbert has given Tsitsipas problems in the past, while Rublev is coming off a semifinal showing in Cincinnati. As for Medvedev, the second-ranked Russian definitely has the most favorable draw of the top contenders (no, Richard Gasquet is not going to be a problem in the first round).

In addition to Tsitsipas vs. Murray, other first-rounders to watch are Alex de Minaur vs. Taylor Fritz, John Isner vs. Brandon Nakashima, Cameron Norrie vs. Carlos Alcaraz, Karen Khachanov vs. Lloyd Harris, and Nikoloz Basilashvili vs. Sebastian Korda.

Ricky contributes to10sballs.com and also maintains his own tennis website, The Grandstand. You can follow him on twitter at @Dimonator.