Men’s Preview: Are we heading for a war of ATP generations at the U.S. Open?

Scanning the men’s bracket at this year’s U.S. Open, it’s easy to see a titanic battle of generations developing at Flushing Meadows in the near future. Or, more precisely, a titanic battle between the haves and the should-haves. Novak Djokovic vs. Marin Cilic, Rafael Nadal vs. Milos Raonic, Stan Wawrinka vs. Nick Kyrgios and Andy Murray vs. Kei Nishikori are all possible second-week matchups. If the next generation is ever going to pull off a mass ambush of the Big Four at a major, this would seem to be the place to do it.

We’ve heard all about ATP revolutions before, of course; here’s a look ahead at how likely this one is.

On Friday, Djokovic said he was still recovering from a left-wrist injury that struck him two days before the Olympics, but he’s doing everything he can to be ready. This is where I would normally say—if he had a tough draw—that he’ll need to be ready right away. But it’s hard to know how sharp Djokovic will need to be against his opening-round opponent, Jerzy Janowicz. The Pole reached the Wimbledon semis in 2013, but is currently ranked No. 228; it’s hard to believe this will be their first meeting. If Djokovic makes it through, he could face a legitimate threat in the next round in Jiri Vesely. The Czech, ranked 48th, handed Djokovic a rare defeat in Monte Carlo this spring.

While Djokovic remains this section’s favorite, Cilic is definitely its dark horse. The No. 7 seed and 2014 Open champion played some of the best tennis of his career to win his first Masters 1000 in Cincinnati last week. Cilic has been playing well for much of this season, but what was impressive in Cincy was the aggressive way he closed out Murray—a player he has had very little success against—in the final. Will there be a new Cilic waiting for Djokovic in the quarters? Jack Sock and Jo-Wilfried Tsonga are the highest seeds that could stand in his way.

First-round all-American matches to watch:

—John Isner vs. Frances Tiafoe

—Sock vs. Taylor Fritz. Sock won in five sets at this year’s Australian Open.

Semifinalist: Djokovic

From one wrist to another. Like Djokovic, Nadal is hoping to have his own ailing left wrist—which kept him out of Wimbledon—ready for his Monday opener. Though his first-round match, against Denis Istomin, looks more cut and dried; they’ve played 11 sets, and Rafa has won 10 of them.

In fact, Nadal’s draw looks more straightforward—a.k.a. easier—all the way through the fourth round. The seeds he could face during that time are Albert Ramos-Viñolas, Lucas Pouille and Roberto Bautista Agut.

Raonic is the No. 2 seed in this section, and his draw also looks manageable, with one exception: He could face 10th-seeded Gael Monfils, who beat him in Toronto earlier this month, in the third round.

First-round matches to watch:

—Raonic vs. Dustin Brown

—Monfils vs. Gilles Muller

Semifinalist: Raonic

I’ve asked it before, but I’ll ask it again: What should we make of No. 3 seed Wawrinka’s chances? It’s always hard to say; as steady as he has made himself at the majors over the last three years, he still doesn’t seem reliable from one day to the next. Can we rely on him to beat Fernando Verdasco in his opener? This is the wrong round to face the Spaniard. He upset the Swiss in the first round at Queen’s this year, and also knocked off Nadal in the first round in Melbourne.

Unfortunately for Stan, his draw may get younger, but not easier, if he does survive Verdasco. He could play Alexander Zverev in the third round, his old friend Kyrgios in the fourth and No. 8 seed Dominic Thiem in the quarters.

First-round match to watch: Wawrinka vs. Verdasco

Possible second-round match to watch: Steve Johnson vs. Juan Martin del Potro

Possible third-round match to watch: Kyrgios vs. Bernard Tomic

Semifinalist: Kyrgios

Who (other than me) said that there aren’t any good first-round matches at majors anymore? The Open men’s draw has its share this year, including Murray’s opening encounter with Lukas Rosol. It may not be competitive—the Scot is 2-0 against the Czech—but it could get testy. In their last match, in Munich in 2015, Murray let Rosol know that, essentially, everyone hates him. Weird fact: Murray has won both of their previous encounters by identical scores (4-6, 6-3, 6-2).

After his titles at Wimbledon and the Olympics, and his runner-up finishes at the Australian Open and French Open, Murray faces only one question here: Can he beat Djokovic? You might think that would make Murray dangerously complacent in his first six matches, and it might. But it also probably won’t matter; he’s won 22 of his last 23, and may be having the best season of his career. Plus, two seeds on his side are Gilles Simon and Feliciano Lopez. Murray is a combined 26-2 against them for his career.

Also here: Kei Nishikori and David Goffin, who are slated to play in the fourth round.

First-round match to watch: Lopez vs. Borna Coric

Question Mark: Grigor Dimitrov

Semifinalist: Murray

Semifinals: Djokovic d. Raonic; Murray d. Kyrgios

Final: Djokovic d. Murray