Aljaz Bedene has been knocked out of the German Tennis Championships following a three-set loss to Karen Khachanov.
British number three Bedene, who enjoyed his best run at Wimbledon this year when reaching round three, went into the match full of confidence after thrashing Jose Hernandez-Fernandez 6-1 6-2 in the first round on Wednesday.
However, the 28-year-old was unable to replicate that type of performance and he lost the first set against Khachanov, whose one and only ATP win came at the 2016 Chengdu Open, in a tie-break, losing 7-4.
Bedene, who is a 19-time winner on the Challenger Tour, battled back to take the next set 7-5 but it was his Russian opponent who produced the goods in the crucial moments, taking the decider 6-4.
Khachanov will now take on Argentina's Federico Delbonis in the quarter-final after the latter recorded an impressive 7-5 6-3 victory over Spaniard David Ferrer, who came into the German event on the back of a Swedish Open triumph.
Elsewhere, world number 40 Benoit Paire was knocked out after losing 6-4 7-6 to 24-year-old Argentine Nicolas Kicker, who has never made the final of any ATP final.
There were also wins for Jiri Vesely, who beat Horacio Zeballos 6-4 6-4, and Philipp Kohlschreiber, who was able to get the better of Gilles Simon in their three-set encounter.