Ben Shelton marked a significant career milestone with his 100th tour-level victory after a hard-fought win over Flavio Cobolli in the fourth round of the Toronto Masters 1000. The 22-year-old American, who has surged into the ATP Top 10 earlier this season, defeated Cobolli 6-4, 4-6, 7-6(1) in a match lasting two hours and 24 minutes.

Shelton’s journey to 100 wins is notable as he becomes the fourth man born since 2002 to achieve this mark and the first U.S. man from that generation to do so. Almost half of his wins have come within the last year, highlighting his rapid progress on the ATP Tour.

The match began with Shelton taking the first set in 51 minutes, but Cobolli fought back to even the match by breaking serve in the second set. In the deciding set, Cobolli gained a 5-3 lead and even served for the match at 5-4. However, Shelton mounted a comeback, winning the next three games to secure a 6-5 lead and eventually dominating the tie-break.

Reflecting on the victory, Shelton said, “Tonight was a long way back with Flavio serving for the match. I’m really happy with this win. It was a fight ’til the end. A really difficult match, and I’m pretty tired right now, but I’m glad we gave you guys a bit of a show.”

This victory advances Shelton to his fourth Masters 1000 quarterfinal, a level where he has yet to move beyond. His previous Masters 1000 quarterfinal appearances were in Shanghai (2023), Cincinnati (2024), and Indian Wells (2025). Next up for Shelton is a match against Alex de Minaur, who earlier defeated Frances Tiafoe.

Shelton’s steady climb and resilience make him a rising contender on the tour, and his ongoing performances at high-tier events underscore his growing stature in men’s tennis.

Taylor Fritz has achieved a milestone no American male player has reached in the ATP Masters 1000 series since its 2009 expansion. The world No. 4 secured a hard-fought victory over Jiri Lehecka in the third round of the 2025 Canadian Open, becoming the first player from outside Europe to reach the quarterfinals of all nine ATP Masters 1000 tournaments.

Fritz, seeded second, battled through a tense, high-quality contest against Lehecka that lasted nearly three hours. The match featured no breaks of serve, with Fritz eventually prevailing 7-6 (7-4), 6-7 (5-7), 7-6 (7-5), saving nine break points to his Czech opponent’s five.

Despite the absence of several top players, including Jannik Sinner, Carlos Alcaraz, and Novak Djokovic, Fritz has emerged as a standout performer in the tournament. Before this run, he had never advanced beyond the third round at this Masters event, but now he stands three wins away from the title.

His achievement places him alongside greats like Djokovic, Rafael Nadal, Roger Federer, Andy Murray, Daniil Medvedev, Alexander Zverev, and Alcaraz, all Europeans who have reached the quarterfinals of all nine events since the series was expanded. Notably, Sinner has yet to reach the Paris Masters quarterfinals.

Fritz has previously made quarterfinals multiple times at Indian Wells (2021, 2022, 2023), Miami (2023, 2025), Monte Carlo (2022, 2023), Cincinnati (2022, 2023), Madrid (2024), Rome (2024), Shanghai (2024), and Paris (2021).

“Making all the Masters quarters is really cool,” Fritz said. “It shows consistency. Today I had to accept that parts of my game were just not there. I was bailed out by a lot of first serves, but I was making too many mistakes.”

Among American players, the challenge of this feat is underscored by the fact that the addition of the Shanghai Masters post-dated players like Pete Sampras and Andre Agassi, who never reached quarterfinals in Monte Carlo, while Andy Roddick never made the Monte Carlo quarters either.

Fritz’s next test comes against sixth seed Andrey Rublev for a place in the semifinals. His win also earned him 150 ATP points, moving him closer to the third spot in the rankings behind Zverev, though overtaking him this week is mathematically impossible.

The American’s focus will soon shift to the US Open, where he must defend 1300 points after finishing runner-up in 2024.

Alexei Popyrin returns to the National Bank Open in Toronto carrying the confidence of a reigning champion and a remarkable nine-match winning streak on Canadian soil dating back to 2024. The 25-year-old Australian admits he doesn’t quite understand why his results have improved here despite a less consistent 2025 season. “I think it’s just good vibes, good feelings from last year maybe,” Popyrin said following his resilient three-set victory over No. 5 seed Holger Rune.

Initially feeling the weight of defending 1,000 ranking points from his title last year, Popyrin opted to embrace the possibility of falling short upon arrival in Toronto, which in turn allowed him to play freely on court. “It’s nice to come in here and kind of accept the fact that if you lose you don’t save the 1,000 points,” he explained. “It’s just a nice feeling to just play free, and that’s what I feel I’ve been doing this week.”

The Australian has demonstrated notable mental toughness this week, overcoming first-set deficits against higher-ranked opponents Rune and Daniil Medvedev, a contrast to his 15-16 win-loss record so far in 2025. His potent serve-forehand combination will be essential as he prepares to face the tournament’s top seed, Alexander Zverev.

Zverev, refreshed from time spent at the Rafa Nadal Academy post-Wimbledon, holds a 3-0 lead in their head-to-head matchups without conceding a set; however, two of those matches date back before 2020, and Popyrin’s progress since then suggests this meeting could be more competitive. The Australian has capitalized on opportunities in Toronto before and will look to do so again against the defensively minded German.

With form, momentum, and belief on his side, Popyrin is poised to challenge Zverev in a compelling encounter at the National Bank Open.