Rafael Nadal was knocked out of Madrid Open quarter-final stage 6-4 6-4 by German Alexander Zverev.
Nadal, a five-time winner in the Spanish capital, was the favorite and top seed having lifted the Barcelona Open trophy last month but played below par on Friday.
Zverev struggled in the opening exchanges, finding himself 4-2 down before breaking Nadal twice to turn the match on its head and take the first set.h
The fifth-seeded German then powered ahead in the second, breaking Nadal’s serve again and holding out to seal a career-first win on clay against the Spaniard.
He will take on third seed Dominic Thiem in Saturday’s semi-final after the Austrian overcame John Isner 3-6 6-3 6-4.
Later Friday, Alexander Bublik of Kazakhstan plays fellow qualifier Casper Ruud from Norway while eighth seed Matteo Berrettini of Italy faces Chilean 16th seed Cristian Garin.