There was a shock in the women's draw of the Kremlin Cup in Moscow as third-seed Agnieszka Radwanska crashed out to Russian Maria Kirilenko.
The Pole had little success on her serve with Kirilenko claiming a straightforward 6-3 6-3 victory against an opponent ranked more than 50 places above her.
Fourth-seed Flavia Pennetta also left the tournament although she was forced to retire while a set up against Agnes Szavay, the Hungarian going through 4-6 3-0.
Sixth-seed Elena Vesnina was another casualty, as qualifier and fellow Russian Evgeniya Rodina triumphed 6-1 3-6 6-2, the 20-year-old making nonsense of the 105 places between the pair in the world rankings.
Eighth-seed Francesca Schiavone, the world No.24, came from a set down to claim a 6-7 (2-7) 6-4 6-3 victory over Nuria Llagostera Vives in two-and-a-half hours in a match littered with errors by both players including eight double faults apiece.
The other match on Wednesday saw Olga Govortsova beat Maria Jose Martinez Sanchez 6-1 6-4.
Meanwhile, Spaniard Anabel Medina Garrigues was a shock casualty at the Luxembourg Open as she was sent crashing out by qualifier Kirsten Flipkens.
Medina Garrigues, the third seed, is ranked almost 60 places above her opponent but that mattered little as the Belgian ran out a 7-5 6-3 winner to move into the third round.
Sixth-seed Sabine Lisicki also safely progressed with a 7-6 (7-1) 6-4 win over wild card Polona Hercog of Slovenia while Timea Bacsinszky defeated Roberta Vinci 6-2 6-2.
In the first round, fourth-seed Daniela Hantuchova thrashed German Tatjane Malek 6-1 6-0 in 52 minutes.
It was by no means a perfect performance by the Slovakian who served four double faults but she had great success on her first serve.
Fifth-seed Yanina Wickmayer also made it through but was pushed harder by Alexandra Dulgheru with the Belgian winning 6-3 7-6 (7-4).
Also through was Lucie Hradecka who beat qualifier Catalina Castano 7-6 (7-4) 6-2.