British number two Dan Evans was knocked out of the Vienna Open in the last eight by Denis Shapovalov in straight sets.
Evans, the unseeded player, struggled after dropping his first serve, and the Canadian eventually won 6-3, 6-3 to advance.
In the eighth game, Evans, 32, did have a break chance that would have tied the first set at 4-4.
But Shapovalov managed to keep him at bay and added to his victory in the first set by winning the second set 3-0.
In the semifinals, he will next face Borna Coric of Croatia.
On Saturday, the other semifinal matchup will be between Daniil Medvedev, the fourth-ranked player in the world, and Grigor Dimitrov, a Bulgarian.