Novak Djokovic vs Kei Nishikori

“Do you have Kei’s number?” a reporter asked Djokovic on Thursday. Djokovic said, yes, as matter of face he does have his number…in his phone. Whether or not the world No. 1 admits it or not, he has Nishikori’s number on court as well; either that or the phrase has no meaning. Djokovic leads their head to head 17-2, and has won their last 16 meetings dating back to 2014. Whatever Kei can do—return, rally, run, change directions with the ball—Djokovic can do better. But Nishikori can hang his hat on one fact: The last time he beat Djokovic, he did it at the US Open, in the 2014 semifinals. Djokovic was strangely flat that afternoon. What are the chances he’s going to let that happen again, with the calendar-year Grand Slam on the line?

Winner: Djokovic

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Rising stars may be stealing the show, but this US Open is all about the Serb's quest for unparalleled greatness.

Rising stars may be stealing the show, but this US Open is all about the Serb's quest for unparalleled greatness. 

Gael Monfils vs. Jannik Sinner

Generations in tennis used to last about five years. Now, with players hanging around longer and longer, they can span up to two decades. Monfils is 34, and Sinner is 20, but they’ve already played two times. Both of those matches were on indoor hard courts in 2019, which was something of an eternity ago in Sinner’s development as a player. The Italian is now ranked four spots higher than Monfils (No. 16 to No. 20), but this match will probably be decided by the Frenchman. His highs are still higher than Sinner’s, and his lows are lower. Monfils has been riding a little bit higher over the course of the last month.

Winner: Monfils

Petra Kvitova vs. Maria Sakkari

Kvitova and Sakkari each play their share of roller-coaster three-setters, so it shouldn’t be surprising that four of their five previous matches have gone the distance. Kvitova leads 3-2, and she won their only meeting at a major, in the fourth round at the 2020 Australian Open. If anything, the stakes will be higher in this one, considering that the Czech and the Greek are in a section headed by Karolina Pliskova and Bianca Andreescu, neither of whom has looked unbeatable so far. In 13 tries, the 31-year-old Kvitova has never reached a US Open semifinal. San she end that streak before it’s too late?

Winner: Sakkari