Hubert Hurkacz vs. Grigor Dimitrov

The Bulgarian and the Pole have been on tour together for five or six years, but this will be their first meeting. Right now it feels as if Hurkacz—ranked 12th, Wimbledon semifinalist—is the man of the moment, while Dimitrov—30 years old, ranked 28th—is a man of the recent past. But that can change quickly with a player of Dimitrov’s talent, as we saw in his three-set win over top seed Daniil Medvedev on Wednesday.

Which portends better things? Hurkacz’s three easy wins so far in Indian Wells, over Alexei Popyrin, Frances Tiafoe and Aslan Karatsev? Or Dimitrov’s one big win, over Medvedev? I’ll take Hurkacz, because he’s less likely to be tired or have a letdown when they get right back out on court on Thursday. Winner: Hurkacz

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Anett Kontaveit vs. Ons Jabeur

Kontaveit and Jabeur have been two of this season’s steady and sometimes-spectacular risers. Jabeur has won 47 matches in 2021 and has her ranking up to No. 14. This summer Kontaveit took home what might have been her most significant title, in Ostrava, with wins over Maria Sakkari, Petra Kvitova, Belina Bencic and Paula Badosa, and earlier this week she knocked out defending Indian Wells champion Bianca Andreescu. When Kontaveit and Jabeur collied two months ago in Cincinnati, the Estonian won in suitably close and entertaining fashion, 7-5 in the third. Look for more of the same from two players who are both finding their groove in their mid-20s, and realizing how far it can take them. Winner: Jabeur

Badosa is clearly enjoying the ultra-slow conditions in the desert.

Badosa is clearly enjoying the ultra-slow conditions in the desert.

Angelique Kerber vs. Paula Badosa

Kerber seems to be enjoying the game at 33 more than she has in recent years, and it shows in her results. More specifically, it shows in her willingness to compete to the bitter end and win close matches; this week she edged Katerina Siniakova, 7-5 in the third set, and Daria Kasatkina, 6-4 in the third. But Badosa is playing better than either of those women at the moment. In her last two matches, the Spaniard has handled two Top 20 opponents, Coco Gauff and Barbora Krejcikova, in straight-set fashion. Badosa will be the attacker and Kerber the defender in this quarterfinal; at 23, Badosa might be a little fresher, too. Winner: Badosa