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Karen Khachanov halted Alexander Zverev in Montreal 2019 for a place in the semi-final. Zverev was among the players to beat at the Canada Open in 2017 and 2018, winning the title and losing to Stefanos Tsitsipas despite building a massive advantage a year later.
Zverev could have played better in 2019, winning only one small ATP 250 title ahead of the Canada Open and standing outside the top-10 in the ATP Race. In Montreal, Alexander prevailed over Nikoloz Basilashvili in a thriller in the third round.
The German stayed on the court for almost three hours and lost steam ahead of the quarter-final clash with Khachanov. Like the German, the Russian had struggled in the opening seven months that year before finding his form in Canada.
Karen beat Alexander 6-3, 6-3 in an hour and 14 minutes for his third Masters 1000 semi-final and the second in a row at this event after losing to Rafael Nadal a year ago.
Karen Khachanov beat Alexander Zverev in the 2019 Montreal quarter-final.
Khachanov toppled Zverev the last time they played at the Paris Masters in the 2018 closing stages en route to the title.
The Russian repeated that in Montreal after losing 13 points in nine service games. Karen fended off both break chances and mounted pressure on the German, who could not endure it. Struggling on the second serve, Alexander played against eight break chances and got broken three times, firing 11 winners and almost 30 unforced errors.
At the same time, Karen counted 17 winners and ten mistakes to master the scoreboard and march on, joining Daniil Medvedev in the first all-Russian Masters 1000 semi-final clash. Zverev was off to a terrible start. He lost serve at love in the encounter's first game after a double fault and took only five points on the return in the rest of the set, unable to erase the deficit and make a turnaround.
Serving at 3-5, Alexander repelled five set points before landing a backhand wide to hand the opener to Karen, who had everything under control in the first part of the encounter. Nothing changed in set number two, as the Russian delivered one good hold after another.
He kept Zverev under pressure and earned a break at love in the sixth game after Alexander's yet another double fault. Zverev finally did something on the return at 3-5, finding his strokes and earning two break chances. Karen stayed calm and denied them, reaching deuce and sealing the deal with a service winner to remain on the title course.