He narrowly took the first set 6-7(2), before going down 7-5 6-4 in the next two.

Belgian David Goffin won over three sets, beating Tunisia's Malek Jaziri 4-6 7-6(4) 6-2.

There was also a straight-sets win for Stefanos Tsitsipas of Greece, who won 7-6(3) 6-4 against Portugal's Joao Domingues.

In the evening's final match, Pablo Cuevas won 6-0 6-7(5) 6-2 against Frances Tiafoe of America.

Germany's Alexander Zverev was eliminated from the BMW Open in Munich after his quarter-final defeat to Chilean Cristian Garin. He lost 6-4 5-7 7-5.

His compatriot Philipp Kohlschreiber fared better, winning 4-6 7-5 6-4 over Matteo Berrettini of Italy.

Spain's Roberto Bautista Agut won 4-6 6-4 6-0 gainst Argentinian Guido Pella.

Italian Marco Cecchinato also won, recovering from losing the first set to beat Hungary's Marton Fucsovics 1-6 7-5 7-5.