Andy Roddick was sent crashing out in the first round of the Madrid Open Monday after being shocked 6-4 6-7 6-3 by Italian qualifier Flavio Cipolla.
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The former world No. 1, seeded 12th at the event, had his serve broken four times by a player listed 148 places below him in the world rankings.
Roddick’s fellow American Mardy Fish was also eliminated at the first hurdle, losing 7-6 4-6 7-6 to compatriot John Isner.
Dutch qualifier Thiemo de Bakker came back from a set down to see off wild ard entrant Juan Carlos Ferrero 2-6 7-5 6-4, while Gael Monfils beat Ivo Karlovic 6-3 7-6.
Marcos Baghdatis was taken all the way by Alejandro Falla, eventually setting up a second-round clash with Rafael Nadal following a 6-3 3-6 7-6 victory.
In the women’s draw, eighth seed Maria Sharapova advanced to the third round after emerging from her all-Russian clash with Ekaterina Makarova with a 6-3 3-6 6-1 win.
Fourth seed Victoria Azarenka had an easy route through to the third round as she defeated Sofia Arvidsson 6-1 6-1m but it was not so straightforward for second seen Vera Zvonareva, as she had to fight back from a miserable start to see off Elena Vesnina 0-6 6-3 6-3.