MADRID, SPAIN - Andy Roddick came up a first-round loser Monday at the Madrid Open, which is a $4.202 million ATP Masters event.

Italian qualifier Flavio Cipolla ousted the 12th-seeded American 6-4, 6-7 (7-9), 6-3 in 3 hours, 2 minutes on the red clay at the Magic Box. This marked Roddick's first ATP clay-court event of the year.

Roddick, who typically does not play his best tennis on clay, has now dropped his last three matches after winning eight straight at one point, including a title in Memphis.

Meanwhile, ninth-seeded Frenchman Gael Monfils topped 6-foot-10 Croat Ivo Karlovic 6-3, 7-6 (8-6), while 6-foot-9 John Isner upended 11th-seeded fellow American Mardy Fish 7-6 (7-5), 4-6, 7-6 (7-3) on Day 2.

Lefthanded Frenchman Michael Llodra leveled American Sam Querrey 6-2, 6-3, while big-hitting Dutch qualifier Thiemo de Bakker overcame former world No. 1 Spanish favorite Juan Carlos Ferrero 2-6, 7-5, 6-4. Ferrero, a wild card this week, was a winner in Madrid back in 2003.

Additional opening-round wins came for Cypriot Marcos Baghdatis, Belgian Xavier Malisse, Spaniard Pere Riba, French qualifier Adrian Mannarino, Ukrainian Sergiy Stakhovsky and Croat Marin Cilic.

In the late contest, Spaniard Daniel Gimeno-Traver dropped the first set but rebounded to best Richard Gasquet 3-6, 6-4, 6-3.

Top-ranked Spanish hero Rafael Nadal beat former world No. 1 Swiss Roger Federer in last year's marquee finale. The two-time Madrid champion Federer was the reigning champ here a year ago.

The reigning U.S. Open, Wimbledon and French Open champion Nadal, Australian Open titlist Novak Djokovic and the 16-time Grand Slam winner Federer are the top seeds here.

Nadal recently titled at the Monte Carlo Masters and in Barcelona. Djokovic is off to a 27-0 start this season, including an Aussie Open title back in January.

The clay-court king Nadal will open his stay in Madrid against the former Aussie Open runner-up Baghdatis.