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Chris Eubanks vs. Soonwoo Kwon

“Look at you, you’re a rock star!” That’s what an old friend of Chris Eubanks shouted when she ran into him on the grounds at the Western & Southern Open in Cincinnati two weeks ago. At the time, a grinning Eubanks was surrounded by autograph hunters and accompanied by security as he walked from the locker room to the courts.

This has been the story of Eubanks’ life since his run to the quarterfinals at Wimbledon. He’s been a star attraction at the four North American hard-court tournaments that have followed. It’s on court where life has been tougher. He went 4-4 in those events, and 0-2 at the Masters 1000s in Toronto and Cincy. Can the Atlanta native find the Grand Slam magic again when he returns to best-of-five in the Grandstand on Monday?

Eubanks is ranked 74 spots ahead of Soonwoo Kwon (30 to 104) and has eight inches on him (6’7” to 5’11”), but he may not relish the chance to face the South Korean. They’re 1-1 head-to-head, and Eubanks had to go five sets to beat him at the Australian Open in January. The American should hope his new fans stick around until this one starts in the early evening; he may need all the help he can get from them. Winner: Eubanks

This has been the story of Chris Eubanks’ life since his run to the quarterfinals at Wimbledon. Can the Atlanta native find the Grand Slam magic again when he returns to best-of-five in the Grandstand on Monday?

This has been the story of Chris Eubanks’ life since his run to the quarterfinals at Wimbledon. Can the Atlanta native find the Grand Slam magic again when he returns to best-of-five in the Grandstand on Monday?

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Stefanos Tsitsipas vs. Milos Raonic

This is a tough first-round draw for both guys. As the seventh seed, Tsitsipas could have expected to face someone far less accomplished than a former Wimbledon finalist. As a player coming back from a long injury layoff, Raonic could have hoped to ease his way back into his first US Open since 2020.

2020 was also the last time the Greek and the Canadian played. Raonic won both of their encounters that year; each time it was on hard courts, and each time it was in straight sets. The 32-year-old is ranked 337th right now, but he has acquitted himself well in his return this summer, winning a match at Wimbledon and beating Frances Tiafoe in Toronto. After a title run in Los Cabos, Tsitsipas didn’t look sharp or confident under coach Mark Philippoussis in Toronto or Cincy, where he went 1-2. Raonic’s strength is his serve, and Tsitsipas’s weakness is his backhand return. It could be a long evening in Armstrong for both men. Winner: Raonic

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Coco Gauff vs. Laura Siegemund

What is Gauff’s reward for hiring a new coach and immediately winning two titles, including the biggest of your career? An opening night session match in Ashe. But no pressure or anything.

Gauff will surely feel some nerves as she walks out in front of an audience eager to see her new and improved game. And her opponent may not help matters. Yes, Siegemund is ranked 108th, 102 spots below Gauff. Yes, she’s 35 years old. But the German won the only previous match between these two, on hard courts in Auckland three years ago. That might not have much bearing on Monday’s rematch, but Siegemund’s current form could. She reached a final earlier this summer in Warsaw, and she should be sharp after winning three qualifying matches in New York.

Which means this match could have its tense moments, and Gauff could have a few shaky ones. But she’s the more consistent player, the much better runner, and the massive fan favorite. That should be enough to get her through. Winner: Gauff