Flavio Cobolli really made Ben Shelton work for his 100th Tour-level victory on Sunday. Not having created a break point since the final game of the opening set, the American would have had to book an early flight out of The Great White North had it not been for a late surge that carried him to a nervous 6-4, 4-6, 7-6(1) victory against the Italian. Shelton knew how close he had cut it.

“Really difficult match. I was down and out, being a break down in the third, the way that he was playing,” he said after the match. “A really difficult opponent for me, someone who’s gotten me in three sets after I’ve won the first set twice,” he added. Well, he’s not going to catch a break from ‘difficult’ opponents anytime soon. As he contends for his first ATP Masters 1000 title in Toronto, the path for him in Cincinnati has already been paved—and the terrain is tricky, to say the least.

When the likes of Carlos Alcaraz and Jannik Sinner withdrew from the Canadian Open, Shelton’s chances of making it to the finish line improved significantly. After all, he is 0 for 3 against Alcaraz and 1 for 6 against Sinner. And chances are that in Cincinnati, he might have to face the ‘SinCaraz’ threat if he manages to have a deep enough run at the event. To begin with, he’s got a bye in the first round. Which means Shelton will kick off his campaign directly in the second round, where he may face the winner between Camilo Ugo Carabelli and Kei Nishikori.

But it’s the third round from where Shelton’s path may really get tough. He might be up against British star Cameron Norrie. The latter had a great run at Wimbledon last month, where he reached the quarterfinals before losing to Alcaraz. In case Shelton manages to beat Norrie, he still won’t be able to catch his breath. Why? In the fourth round, the American may go up against Russian star Daniil Medvedev. And if the American gets past him, too, he will likely face World No.3 Alexander Zverev, who, in fact, bested him last season in Cincinnati. However, the road to the final will only get scarier for Shelton even if he wins against the German pro, as Carlos Alcaraz may be waiting for him in the semis. And if that’s not enough, the summit clash may pit him right in front of World No.1 Jannik Sinner (provided Shelton actually beats the Spaniard).

Speaking of Shelton’s track record at the Cincinnati Open, it’s gradually improved lately. Back in 2022, he made his event debut and reached the round of 16. A year later, he couldn’t move past the round of 32. But last season, the American made a solid impression and succeeded in entering the quarterfinal stage. As of now, there’s still time for his next challenge to begin. Before that, Shelton has business to attend to in Toronto.

Ben Shelton reaches the semis at the Canadian Open for the first time

On Tuesday night, Ben Shelton edged out Australia’s Alex de Minaur in the quarterfinal battle in straight sets (6-3, 6-4). With that, the 22-year-old confirmed his maiden semifinal appearance at an ATP Masters 1000 tournament. It’s a huge occasion for him, considering how in the previous two campaigns in Toronto (2023 and 2024), he had failed to move past the round of 32. This time, however, the youngster seems determined.

After defeating de Minaur, Shelton has also become the youngest Masters 1000 semi-finalist in two decades. Thanks to his lethal serve and fantastic forehand, the American didn’t give his opponent any chance, taking just 91 minutes to wrap up this encounter, hitting 11 aces.

Now, he will be up against compatriot Taylor Fritz in an all-American semifinal on Wednesday. He’s coming off his straight-set QF win over Andrey Rublev. Fritz currently leads the H2H tally 1-0. In their only meeting in 2023, Fritz emerged victorious during the R64 in Indian Wells. It will be intriguing to see if Shelton takes his revenge this time to settle the score.