Alex Michelsen reaches first Masters 1000 quarterfinal in Toronto, Karen Khachanov awaits

In a clash between friends and countrymen, 20-year-old Alex Michelsen defeated 19-year-old Learner Tien in straight sets in the fourth round of the National Bank Open on Saturday, 6-3, 6-3.

With that, Michelsen is into the 15th and biggest quarterfinal of his career. It's his first quarterfinal at the Masters 1000 level.

He’s also the youngest American to reach a Masters 1000 quarterfinal since Sebastian Korda at Miami in 2021, and the youngest American man to reach the last eight in Canada since Andy Roddick in 2003.

“It feels really good,” he said. “It’s uncharted territory from this point on, and I’m super happy to be in the quarters for the first time.”

Michelsen was out in front against Tien from the start, jumping out to an early 3-0 lead and riding that break to the first set. He even broke in the first game of the second set—Tien got that break back and held for 2-1, but Michelsen won five of the next six games to close it out.

“We’re very, very close friends, and we’ve been talking and sending each other memes just like normal,” Michelsen said. “We’ve grown up together, coming from when we weren’t very good and now we’re playing in the round of 16 of a 1000, so it’s super special.

"I knew that one of us was going to be in the quarterfinals here, so I was super happy stepping onto the court today.”

Awaiting the No. 26-seeded Michelsen in the quarterfinals will be No. 11-seeded Karen Khachanov, who took out No. 8-seeded Casper Ruud in the second fourth-round match of the day, 6-4, 7-5.

Ruud had won both of the pair’s previous meetings, including a very high-profile encounter in the semifinals of the US Open three years ago, but Khachanov was too good this time, originally leading by a set and a break at 6-4, 4-2 before Ruud won three games in a row and looked like he might be forging a comeback—but Khachanov won the next three games, losing only one point, to run away with it in the end.

“I was controlling the match, trying to play aggressively, and my game plan was working,” the world No. 16 said afterwards. “It became a little bit difficult in the second set, but I’m so glad that in the end I was able to pull through and break him one more time.”

Khachanov finished with a clean 29 winners to 23 unforced errors, with more than half of those winners (15) coming off his forehand alone.

He’s now through to his milestone 10th Masters 1000 quarterfinal, and his third in Canada—he was a semifinalist here in 2018 and 2019.

Michelsen and Khachanov have met once, with the American winning in the third round of the Australian Open this year, 6-3, 7-6 (5), 6-2.