Three To See, Madrid: May 7

(9) Janko Tipsarevic vs. Juan Monaco
Head-to-head: Tipsarevic leads 3-2

You might think the tattooed Tipsarevic makes his biggest mark on hard courts, but the Serb joined David Ferrer as one of only two men to win 20 matches on both hard and clay courts last season. Tipsarevic beat Gilles Simon and Novak Djokovic back-to-back to reach the 2012 Madrid semifinals a couple of months before the he beat Monaco, 6-4, 5-7, 6-3, in the Stuttgart final.

Since starting the season on a skid of five straight opening-round losses, Monaco has won six of his last nine matches—all on clay. He’s also won two of three clay-court meetings with Tipsarevic.

Coming off consecutive clay-court quarterfinals, Tipsarevic should be confident; he is the more aggressive player and bigger server. But Monaco knows his way around the dirt, winning three clay-court titles and scoring a couple of Top 10 wins on clay during the past year. I see him grinding out a close win.

The Pick: Monaco in three sets

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Three To See, Madrid: May 7

Three To See, Madrid: May 7

(11) Nadia Petrova vs. Svetlana Kuznetsova
Head-to-head: Kuznetsova leads 5-2

Former Russian Fed Cup doubles partners face off for the first time in three years. Petrova is pushing for a Top 10 return; Kuznetsova is playing to raise her ranking for a French Open seeding.

The 40th-ranked Kuznetsova has already won 20 matches this year and she's been resilient in three-setters, winning nine consecutive matches. Petrova is 3-2 when going the distance this season.

Former French Open champion Kuznetsova’s expansive all-court game can sometimes create tactical confusion: She hits with plenty of topspin and can camp out behind the baseline and grind down opponents on slow surfaces, or she can flatten out her shots and use her net skills to close in the front court when she chooses.

Petrova’s two-handed backhand and her serve can both be imposing shots, but Kuznetsova has a clear edge on the forehand side, as Petrova’s western-grip forehand can sometimes go askew under pressure. If Kuznetsova plays with patience and imposes her advantage in the forehand pattern, I see her advancing.

The Pick: Kuznetsova in two sets

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Three To See, Madrid: May 7

Three To See, Madrid: May 7

Andreas Seppi vs. (13) Tommy Haas
Head-to-head: Tied 1-1

Top 20 players coming off productive weeks meet for the third time. Seppi was a semifinalist at the Portugal Open last week, while Haas defeated defending champion Philipp Kohlschreiber to capture his 14th career title in Stuttgart.

Haas can do a little bit more with the ball—he has a flair for unsettling opponents with his varied pace and spins, particularly off his versatile one-handed backhand—while Seppi is an extremely steady and fit player.

The 35-year-old Haas seems to be thoroughly enjoying his late-career renaissance: He’s won 13 of his last 17 matches, including three wins over Top 15 opponents in that surge. While the combination of a letdown after Haas’ title run and Seppi’s consistency style can create challenges, the German has more options. If he manages the match wisely, he should get through.

The Pick: Haas in two sets