Stefanos Tsitsipas and Denis Shapovalov headline throwback clash | Indian Wells, Day 1

Jenson Brooksby vs. Alexei Popyrin

Hopefully this match will be taking place in Indian Wells, rather than in Dubai. Brooksby and Popyrin both played in the UAE last week, but presumably they were able to evade the flight ban and make it out over the weekend.

Their first head-to-head encounter should make for an entertaining show in the intimate confines of Stadium 4 on Tuesday afternoon. The American and the Australian are close in the rankings—41 for Brooksby, 44 for Popyrin. And while neither has put together a string of wins yet in 2026, each brings a lot of big-swinging, highly-vocal competitive aggression to the court. Neither, it seems likely, will avoid fist-pumping in the other’s face.

Popyrin has the superior shots. He has a bigger and heavier-spinning serve, and his forehand will be the most lethal weapon on the court. Brooksby is the better point-constructor and the more stubborn competitor, and he’ll do what he can with his variety of chops and sidespin to disrupt the 6’5 Popyrin by making him stretch and bend and get low.

Brooksby is a California native who has reached the round of 16 at Indian Wells twice. He may be the second-best ball-striker on court, but he should still be in his element. Winner: Brooksby

Read More: Indian Wells Men's Preview: Will Carlos Alcaraz and Jannik Sinner meet again?

Stefanos Tsitsipas vs. Denis Shapovalov

Does seeing these two names take you back to the late 2010s, to the Before Times, to the age of the Next Gen? There’s a good reason for that.

Tsitsipas, now 27, and Shapovalov, now 26, faced off four times from 2018 to 2020. In those days, the Greek was just out of his teens, and already in the Top 5. The Canadian was younger still, but trending toward the Top 10. Each featured a throwback one-handed backhand, and showed a knack for playing dynamic, attacking tennis. Tsitsipas announced himself with an upset win over Roger Federer in Australia, and Shapo did the same by stunning Rafael Nadal at home in Montreal. Back then, their head-to-head encounters had ramifications for the future of the ATP.

Two of those early matches were close—7-6 in the third in Miami in 2019, and 7-6, 7-6 at the ATP Cup in 2020. Perhaps surprisingly, it was the lower-ranked Shapovalov who won both times, and who still has a 4-2 edge over Tsitsipas in their head-to-head. In fact, Shapo is 4-0 on hard courts, and won their last meeting, a year ago in Miami, 6-2, 6-4.

Now there’s a lot less buzz when they meet. Shapo is ranked 39th, Tsitsipas is 43rd. Neither is seeded, so here they are on Day 1. I’d say each of them paid a price for using that throwback one-hander; their opponents pick on that shot, especially with their serves. Tsitsipas is 9-5 this season; Shapo is 4-4, though he did make the semis in Dallas.

Shapo is terminally streaky, but his winning record against Tsitsipas may indicate that he can use his serve and forehand to steer more of the rallies into the Greek’s backhand. Either way, even if their rankings aren’t what they used to be, their brand of athletic shot-making never goes out of style. Winner: Shapovalov

Sloane Stephens vs. Camila Osorio

Stephens says her career keeps getting “weirder and weirder.” And it was something of a surprise, at least to me, to see her name in a draw again. She’s 32 and ranked 780th, and she missed most of last year with a stress fracture in her right foot. In the past, she was also someone who could have mixed feelings about the tennis life. But here she is, waiting out an injury, ready to go again. It hasn’t been all that long—2024—since she won her last title.

You might think a night match in Indian Wells, with its supportive fans and slow, bouncy hard courts, would be a good time and place for the clay-loving Sloane to make some progress in her comeback. But she’s just 13-13 in the desert, and has made just one quarterfinal here in those 13 tries. It’s also hard to say whether Osorio, a 24-year-old Colombian dirt-baller, qualifies as a favorable draw for Stephens or not. The two have never played, and while Osorio doesn’t thrive on hard courts, she does have one very good memory from Indian Wells. Last year she knocked off Naomi Osaka 6-4, 6-4 in a night match here.

Osorio is 10-5 this year, and has a 125-level title. She’s somewhat undersized at 5’7, and this will probably be a war of topspin attrition. But she’s ranked more than 700 spots than her opponent at the moment. That might end up counting for something. Winner: Osorio