Former champion Igor Kunitsyn crashed out in the qualifying rounds of the Kremlin Cup to a player ranked nearly 500 places below him on Sunday.
The joint WTA and ATP event starts Monday in the Russian capital, and has attracted more stars of the women's game than that of the men's.
Kunitsyn shocked Marat Safin to take the 2008 crown but the 30-year-old, ranked 149 in the world was beaten 6-3, 3-6, 6-3 by compatriot Richard Muzaev, who is No. 624.
That 2008 win is Kunitsyn's only title to date. The next year he enjoyed his career-high ranking of 35.
Muzaev goes on to face Evgeny Korolev of Kazakhstan for a place in the main draw.
A total of eleven Russians are in the both the men's and women's draw so far.
Sixteenth-ranked Maria Kirilenko leads the charge in the women's draw as fifth seed, and three-time champion Nikolay Davydenko leads five men.
The top four seeds for the WTA event are Sam Stosur, Marion Bartoli, Caroline Wozniacki and Ana Ivanovic. On the men's side, they are Alexander Dolgopolov, Andreas Seppi, Viktor Troicki and Thomaz Bellucci.
All eight have byes into the second round.