Three to See, US Open Day 6: Can Botic van de Zandschulp carry out another upset over Jack Draper? 

Daniil Medvedev vs. Flavio Cobolli

Coming into the Open, few, if anyone, guessed that Carlos Alcaraz would be out of the event before Daniil Medvedev. It was the Russian, rather than the Spaniard, who was the high seed most likely to make an early exit. The “hard-court specialist” had arrived having lost two straight opening-round matches on hard courts in Montreal and Cincinnati. There was speculation about his service yips, about injuries, about post-Olympic exhaustion. But here he is, having dropped one set in two matches, while Alcaraz is heading home.

Medvedev still hasn’t answered all of the questions, especially those concerning his serve. He double-faulted 10 times in three sets in the second round, and made just 47 percent of first deliveries. That would give an opening to just about any third-round opponent at a Slam, including Flavio Cobolli.

Medvedev has never played or practiced with the Italian. All he can go on is the eye test.

“I saw him play. He has, I think, really explosive tennis,” Medvedev said.

He has that part right. The 22-year-old, 31st-ranked Cobolli plays with a loose-armed abandon that feels new on tour. It has taken him a bit of time to get weapons under control. Perhaps surprisingly for an Italian, it has happened on hard courts this summer. He made the Citi Open final, beat Felix Auger Aliassime in Montreal, and beat Tommy Paul in Cincinnati.

Medvedev has the albatross-like defensive and disruptive skills to frustrate Cobolli. But if his serve is still subpar, it will be a much tougher task. Winner: Medvedev

Jack Draper vs. Botic Van de Zandschulp

The problem with pulling a stunning upset early in a major is that you don’t get a trophy for it. Your reward is another match two days later, typically on a side court instead of center stage. Once upon a time, fans of Roger Federer liked to keep track of all the times that a player who knocked off the Maestro at a major was then quietly ushered out in the next round.

Will the conqueror of Carlos Alcaraz suffer the same fate on Saturday? Van de Zandschulp was nothing short of brilliant for three sets against the Spaniard. He not only out-hit him, he out-ran him, too. Can he do it again? The fact that he has been a quarterfinalist at the Open three years ago makes me think it’s possible, because he really like these courts. But the fact that he’s ranked 74th, and Draper is seeded 25th, makes me think it’s less likely.

The two men have never played. Both, naturally, swing big and hit hard. Draper does it from the left side, and his serve may be a little more effective for that reason. But Van de Zandschulp hits flatter,  heavier ground strokes, which may be better suited to this surface. If Alcaraz can’t do anything with his game, how will Draper?

The X-factor may be Van de Zandschulp’s mindset. He had nothing to lose at the start against Alcaraz, which allowed him to swing freely early, and build confidence. If he can play with that freedom against Draper, he can win. But I’m going to say the task won’t feel quite as simple this time around. Winner: Draper

Iga Swiatek vs. Anastasia Pavlyuchenkova

Hopefully, the first meeting between these two won’t be a guide to how how their second match will go. Last spring, the 23-year-old Pole and the 33-year-old Russian met in Rome…and parted ways quickly. Swiatek won 6-0, 6-0. We might be tempted to excuse the result because it came on Iga’s favorite surface. But Pavlyuchenkova, a finalist at Roland Garros in 2021, likes dirt, too.

The fact that Swiatek won her second-round match at the Open 6-0, 6-1 also wouldn’t seem to bode well for this one. But there are a couple reasons to hope for more from Pavlyuchenkova. She’s coming off one of her better results in recent years, a quarterfinal appearance in Cincinnati that included a win over Zheng Qinwen. Pavlyuchenkova also hits with pace from both wings, which gives her a chance to rush Swiatek on her forehand side. If there’s a weakness in Iga’s game, most opponents find it there. Winner: Swiatek