(Photo credit: John E. Sokolowski-Imagn Images)

One point away from defeat, 11th-seeded Karen Khachanov escaped to defeat top-seeded Alexander Zverev 6-3, 4-6, 7-6 (4) on Wednesday in the semifinals of the National Bank Open in Toronto.

The result is arguably the biggest for the 29-year-old Russian in nearly seven years.

Khachanov is through to the final of an ATP Masters 1000 event for just the second time, following his championship at the Paris Masters in 2018. Four other times he was a Masters 1000 semifinalist, including at the Canadian event in 2018 and 2019.

His best results at Grand Slam tournaments were semifinals losses at the 2022 U.S. Open and the 2023 Australian Open.

Khachanov will oppose a U.S. player in the championship match. Second-seeded Taylor Fritz and fourth-seeded Ben Shelton squared off in the second semifinal late Wednesday night.

Zverev had a match point at 5-6 on Khachanov's serve in the third set, but the German came up short in a bid to reach his first Masters 1000 final of the year. Zverev won Masters 1000 tournaments in Rome and Paris in 2024.

Down 3-1 in the third-set tiebreaker, Khachanov won the next five points, then sealed the victory on his second match point.

'I had to dig deep and lift my level,' Khachanov said. 'It was a very demanding, very mental, very physical match. So I'm very happy to get the win after losing some easy ones to him in recent years.

'Today was a real close one. I was match point down. If the ball touches the net and drops over, we wouldn't be talking now.'

The match stats weren't impressive, as both players had more unforced errors (44 for Zverev, 34 for Khachanov) than winners (36 for Zverev, 29 for Khachanov).

Khachanov owns two wins in three career matches against Fritz, though the American won their most recent (and most important) contest, prevailing in four sets in the Wimbledon quarterfinals last month.

Shelton beat Khachanov in their lone matchup, during the third round at Indian Wells, Calif., this spring.

--Field Level Media