Kyle Edmund falls to shock defeat to Portuguese qualifier Joao Domingues at Estoril Open
Edmund, seeded seventh, lost the opening set 6-4 and despite battling back to take the second 6-3, crashed out after the Portuguese qualifier won a tie-break in the decider.
The victory was Domingues' first on the ATP Tour and will send the world No 242 to a new career high ranking.
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Hide AdFor world No 41 Edmund, it represents a brief knock-back in his attempts to break into the coveted world's top 32 ahead of the French Open.
The Yorkshireman was a clear favourite heading into the match and has been in good form since the start of the clay-court season.
The 22-year-old took Rafael Nadal to three sets at the Monte Carlo Masters last month before running into finalist Dominic Thiem in the second round of the Barcelona Open last week.
Elsewhere, Britain's Aljaz Bedene beat Hungary's Marton Fucsovics in the first round of the Istanbul Open.
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Hide AdThe 27-year-old won 7-6 (7-3) 4-6 6-4, just two days after losing to Lucas Pouille in the Hungarian Open final.
The British number four will play top seed Milos Raonic for a place in the quarter-finals.