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Coco Gauff vs. Caroline Dolehide

Gauff has a new hair color—blond—and a new seeding: No. 2. This is the first time she’s been that high at a major. One big benefit is already obvious: She’s not in the same half of the draw as Iga Swiatek.

But Iga is far in Coco’s future. On Monday, last up in Centre Court, she’ll be facing Dolehide, a fellow American ranked 51st.

Dolehide, 25, has never won a main-draw match at Wimbledon, but she has always been a strong ball-striker with a full-cut Western forehand and two-handed backhand. Despite her record at the All England Club, her game should be a good fit for grass; two weeks ago she came out of qualifying to reach the quarters in Birmingham. While she’s 0-2 against Gauff, three of the four sets they’ve played have been 7-5 or closer.

Gauff went out in the first round at Wimbledon last year, to Sofia Kenin, a loss that spurred her to hire Brad Gilbert as her coach. Since then she has made the semis or better at the last thee majors. Another first-round defeat seems unlikely, but this could be a test worth having. Winner: Gauff

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Naomi Osaka vs. Diane Parry

Osaka will make her first appearance at Wimbledon since the Before Times: 2019, to be exact. She was just 4-3 at the event before that, and she has never made grass a priority. Her coach, Wim Fissette, has said in the past that she was nervous about falling on it.

Now Osaka and Fissette both say those days of uncertainty and ambivalence are over, and they’re all in on grass. This summer she has played two tournaments on the surface, and gone 2-2. If that isn’t reason to hope for something better at Wimbledon, her near-win over Iga Swiatek in Paris last month surely is.

Osaka and Parry will meet for the first on Court 2 in the late afternoon. Parry is an undersized but talented 21-year-old Frenchwoman currently ranked 53rd. Like a lot of her countrymen and women, she has good grass instincts. She’s 3-2 at Wimbledon in two appearances, and she made the semifinals in Nottingham earlier this month. Parry has the hands and court sense to make this a match, but may not have the firepower to win it. Winner: Osaka

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Matteo Berrettini vs. Marton Fucsovics

On paper, there are a dearth of competitive or high-profile first-round matches on the men’s side. But this bruising, brute-force encounter will offer a little star power, and may give us some suspense, too—especially for a match that will go off early on relatively obscure Court 12.

The Italian made the final at Wimbledon in 2021, and if he wins this match, he’ll likely face top seed and countryman Jannik Sinner next. As for the Hungarian, he’s 32 and has slipped to No. 69 in the rankings, but he’s 1-0 against Berrettini, has been to the quarterfinals at Wimbledon, and can hold his own in the physicality department with anyone.

Berrettini will surely want to make the most of his chance to get back on these courts. He has been considered a dark-horse favorite to win the title on a couple of occasions, and his trip to the final in Stuttgart three weeks ago shows that, despite his litany of injuries, he’s still a very tough out on grass. The prospect of facing Sinner should be motivation enough for him on Monday. Winner: Berrettini