Andrey Golubev of Kazakhstan beat Safin 6-4, 6-2 to advance to his first career quarterfinal.
Safin, the 31st-ranked Russian who has twice won the tournament, had trouble on his serve, winning only 15 of 51 returned points.
The 150th-ranked Golubev, who reached the second round of the U.S. Open in September, broke Safin in the fifth game of the first set but double-faulted three times in the next game to drop serve and stay level at 3-3.
In the ninth game, Safin saved three break points with aces but was broken on the third deuce, and Golubev served for the set.
"The second break in the first set was a decisive one," Safin said. "He became confident and it was much more difficult to play against him. In fact, I didn't have many chances in the second set."
Golubev won five consecutive games for a 5-1 lead in the second set.
"I knew he would be playing his best tennis today," Safin said. "He had nothing to lose and played with no problems. No matter how I tried, it was his day today."
"He (Golubev) totally deserved his victory," Safin told reporters. "He served better than me, was more consistent from the baseline and made less mistakes."
Golubev, born in Russia before switching his alliance to Kazakhstan, said: "Marat was my hero when I was growing up. It was my dream to play him and I couldn't even imagine beating him."
Later today, Marat Safin and Igor Kunitsyn were beaten by R. Bopanna and M. Mirnyi in the doubles.
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