Updated

Second-seeded Andy Roddick lost to 2, 6-4 on Friday at the $531,000 SAP Open.

Roddick. a three-time San Jose titlist (2004-05, 2008), was the highest seeded player remaining in the field after top-seeded Frenchman Gael Monfils withdrew earlier this week due to a right knee injury.

Istomin advances to take on fifth-seeded Frenchman Julien Benneteau, who defeated Belgium's Steve Darcis, 3-6, 6-1, 6-2, in the nightcap on the hardcourts at HP Pavilion.

In other action on Friday, defending SAP Open champion Milos Raonic of Canada defeated South Africa native Kevin Anderson, the No. 6 seed, 7-5, 7-6 (7-3). Raonic was tested in his quarterfinal matchup, but the third seed held on, moving one step closer to repeating as champion in San Jose, where he knocked off Spaniard Fernando Verdasco in last year's final.

Raonic will meet American Ryan Harrison in the semifinals. Harrison made quick work of Dimitar Kutrovsky, defeating the Bulgarian, 6-1, 6-4, in just over an hour in the first matchup of the day on Friday.

This year's SAP Open champion will earn $95,860.