British number two Dan Evans bowed out of the Vienna Open after a straight-set defeat to Denis Shapovalov in the last eight.
Unseeded Evans struggled after losing his opening serve as the Canadian progressed with a 6-3 6-3 victory.
Evans, 32, did have a break point in the eighth game that would have levelled the first set at 4-4.
But Shapovalov held him at bay and built on his first-set success by taking a 3-0 lead in the second.
He will next meet Croatia’s Borna Coric in the semi-finals.
World number four and top seed Daniil Medvedev and Bulgaria’s Grigor Dimitrov will contest the other last-four tie on Saturday.
