Casper Ruud became the latest seed to crash out of Munich's ATP tournament on Friday after he was beaten in straight sets by Botic van de Zandschulp of the Netherlands in the quarterfinals.
After a tight opening set on clay, the eighth-seeded Van de Zandschulp cruised past Norway's Ruud to seal a 7-5, 6-1 win and a place in Saturday's semifinals.
"Maybe the score is easier than it really was," said van de Zandschulp, who will face Serbia's Miomir Kecmanovic in the last four.
"The first set was really tight, the second set was a little bit easier, but I think I played really well."
Ruud, seeded second in Munich, had been the favourite after Germany's Olympic champion Alexander Zverev lost in the second round to Danish teenager Holger Rune.
The 18-year-old wildcard progressed into the semi-finals in Munich after Rune sealed a 6-0, 6-2 win over Emil Ruusuvuori of Finland on Friday.
He next plays Germany's Oscar Otte, who is into his first semi-final on the ATP tour after a 6-1, 7-6 (7/1) win against Chile's Alejandro Tabilo.
Kecmanovic earlier cruised into the last four with a 7-6(5), 6-2 win against fourth-seed Nikoloz Basilashvili, the defending champion in Munich.
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