Alexander 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 did not play that well 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, staying on the court for almost three hours and losing steam ahead of the quarter-final clash with Karen Khachanov. Like the German, the Russian had struggled in the opening seven months that year before finding the 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, losing to Rafael Nadal a year ago.
Karen Khachanov beat Alexander Zverev in the 2019 Montreal quarter-final.
Khachanov toppled Zverev last time they played at the Paris Masters in the closing stages of 2018 when he won the title.
The Russian repeated that in Montreal, losing 13 points in nine service games and fending off both break chances to mount the pressure on the German, who could not endure it. Struggling on the second serve, Alexander had to play 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-ever all-Russian Masters 1000 semi-final clash. Zverev was off to a terrible start, losing serve at love in the first game after a double fault and taking 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 Khachanov, who had everything under control in the first part of the encounter. Nothing changed in set number two, with the Russian delivering 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. Returning to stay in contention at 3-5, Zverev finally did something more outside his serve and created two break points, denied by Karen, who sealed the deal with a service winner to stay on the title course.