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“It’s always a question of what you do in those important moments when it counts,” he said.

It was Khachanov’s first win over a top-10 opponent in four tries this season.

Khachanov will next face the winner of the late semifinal between Americans Taylor Fritz and Ben Shelton. The start of the match was delayed for about 15 minutes due to a technical issue with the electronic line-calling system. 

The final was scheduled for Thursday night. 

Both Khachanov and Zverev showed off their big service games early in their match on a warm, hazy evening at the York University venue. 

Extended rallies were rare over the early going as players settled in on the fast hardcourt. 

Khachanov took advantage of 11 unforced errors by Zverev in the first set but the German broke serve at love to take the second set. 

Zverev, the world No. 3, appeared to fade in the third-set tiebreaker while the 16th-ranked Khachanov continued his steady play. 

“The first set was terrible,” Zverev said. “I kind of gave him a headstart and he’s too good to not use that.”

Fritz, meanwhile, is seeded second and ranked fourth. Shelton is the fourth seed and world No. 7.

Their match will be the first all-American semifinal at an ATP Masters 1000 tournament since Mardy Fish beat Andy Roddick in 2010 at Cincinnati.

Earlier in the day, sixth-seeded Joe Salisbury and Neal Skupski posted a 7-6 (5), 6-2 doubles semifinal win over Maximo Gonzalez and Andres Molteni of Argentina.

Salisbury and Skupski will face fellow Brits Julian Cash and Lloyd Glasspool, the No. 2 seeds, in Thursday’s final.

This report by The Canadian Press was first published Aug. 6, 2025. 

Read more on the National Bank Open at thestar.com