Robin Haase defeated defending champion Andrey Rublev to book his place in the semi-finals of the Croatia Open Umag.
After reaching the semi-finals of a WTA Tour event for the first time since 2016, Eugenie Bouchard received further good news.
Fabio Fognini will meet Fernando Verdasco in the semi-finals of the Swedish Open after they both won in straight sets on Friday.
Spanish veteran David Ferrer – a three-time winner and this year's seventh seed – was beaten 7-5 6-2 by Caser Ruud.
Eugenie Bouchard is in position to challenge for the Ladies Championship Gstaad as the seeds tumble.
A three-time finalist at the Hall of Fame Tennis Championships, Ivo Karlovic suffered a second-round loss.
Pablo Carreno Busta and Fernando Verdasco will meet in Bastad but top seed Diego Schwartzman was knocked out on Wednesday.
Romanian Mihaela Buzarnescu thrilled her home crowd by rallying in the second set to beat Tamara Zidansek in Bucharest.