Each day during the French Open, we'll preview—and predict the winner of—three of the most compelling men's matches.

(13) Juan Monaco vs. (19) Milos Raonic
—Head to Head: Never played

This match may come down to who can most impose their style: Raonic will try to enforce his explosive attacking game, while Monaco aims to counter the Canadian into submission. Interestingly, Raonic’s tennis idol is Pete Sampras, while Monaco grew up admiring the American's chief rival, Andre Agassi, and it’s clear how both Hall of Famers have influenced their respective games.

The big-serving Raonic certainly has the weapons to win this match; the question is, can Monaco mute them by winning rallies of attrition? The 15th-ranked Argentine has won clay-court titles in Vina del Mar and Houston this season, and enters the third round with a 15-4 record on clay in 2012. Raonic has trained on dirt in Spain and put that good work to use in Barcelona, sweeping Nicolas Almagro and Andy Murray in succession to reach semis. He also pushed eventual champion Roger Federer to a third-set tiebreaker in Madrid.

The weather could play a factor here: If it’s a humid day and the court is slow, that should help Monaco, while Raonic will relish faster conditions. Monaco is the more experienced clay-courter, but Raonic is a Top 10 talent with immense upside.

The Pick: Raonic in four sets.

(8) Janko Tipsarevic vs. (29) Julien Benneteau
—Head-to-Head: Benneteau leads 1-0

The 30-year-old Frenchman’s appearance in the third round is a victory of sorts, considering an elbow injury suffered in Monte Carlo sidelined him until this week. Because his return was uncertain, Benneteau may may come out swinging freely and feeling less pressure than his higher-ranked opponent. Benneteau won their only prior meeting in four sets in the first round of the 2006 French Open, and went on to reach the singles and doubles quarterfinals that year, but Tipsarevic is a much more complete and confident player now.

This is an interesting match because both men can do a little bit of everything, and both are capable of serving with authority. Tipsarevic is playing for his first French Open fourth-round appearance, and showed his clay-court skills in beating Gilles Simon and Novak Djokovic back-to-back in Madrid. Clay is not his favorite surface, and he’s played more matches in recent weeks, but he's a bit quicker around the court than Benneteau, giving him an edge.

The Pick: Tipsarevic in five sets.

(17) Richard Gasquet vs. Tommy Haas
—Head to Head: Haas leads 2-1

If you saw Gasquet’s gripping win over Grigor Dimitrov in the second round, you experienced the joys of the one-handed backhand. Another superb single-hander will be on display when the 34-year-old German tries to stretch his five-match winning streak (Haas won three matches in qualifying) against the gifted but enigmatic Frenchman. This is their first meeting on clay and their first clash since Haas held off Gasquet in five sets at the 2008 U.S. Open.

Though Haas has been efficient in dropping just one set, match-to-match recovery can be unpredictable on clay—especially at his age. The younger Gasquet has some liabilities, though: He can be fragile under pressure—he played a very tight game to drop serve late in the first set against Dimitrov, but won in four—and the fact he routinely gives up so much ground behind the baseline makes him vulnerable to Haas’ short slice and net play. But Gasquet has the game to win this match, if he can stay out of his own way and withstand the pressure of expectation from the French fans. A win would send Gasquet into the fourth round for the fourth time in his last five majors.

The Pick: Gasquet in four sets.