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Dominic Thiem's wait for the first win of his comeback goes on after he lost to Benjamin Bonzi at the Estoril Open.
Thiem was competing in just his second tour-level event of 2022 after suffering a wrist tear last June, having lost to John Millman at the Serbia Open last week.
The 2020 US Open champion could not find a way through against Bonzi, who did not face a break point in prevailing 6-3 7-6 (11-9).
Bonzi will next face Sebastian Korda, the eighth seed a straight-sets winner over Pierre-Hugues Herbert.
Fifth seed Frances Tiafoe and sixth seed Albert Ramos-Vinolas defeated Dusan Lajovic and Jordan Thompson respectively, but seventh seed Tommy Paul lost to veteran Richard Gasquet.
At the BMW Open in Munich, sixth seed Dan Evans lost in his first match for the fourth time in five tournaments.
The sixth seed was beaten 6-4 6-4 by Maxime Cressy, while there were wins for Hugo Gaston, Ilya Ivashka and Oscar Otte.