Cameron Norrie slipped to a straight-sets defeat against Karen Khachanov in the opening round of the Monte Carlo Masters.
Norrie, playing on clay for the first time since February, started well and struck with the first break of the match but eventually went down 7-5 7-6 (3).
Khachanov broke straight back in the opening set and toppled the Norrie serve again at 6-5 to avoid a first-set tie-break.
Both players broke each other at the start of the second set and Norrie looked again to be in control when he went 5-3 ahead.
But once again Khachanov broke back when it mattered and took the tie-break 7-3.
Dan Evans suffered a straight-sets defeat to Sebastian Ofner as his struggles at the start of the clay-court season continued.
Evans’ second match on the surface this term was over quickly after he was blown away by the Austrian.
The British number three dropped the first four games en route to a 6-1 6-4 defeat.
Evans had lost his first clay-court match of the season in straight sets to Roberto Carballes Baena at the Grand Prix Hassan in Marrakech last week.
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