In Shanghai last year, Roger Federer described his decision to enter last week’s tournament in Estoril, Portugal, as part business, part pleasure. Because the largest events on clay now uniformly give byes in the first round to top players and no longer require best-of-five-set finals, he said, he would enter a smaller event to make sure he had the proper preparation for Roland Garros in Paris. He added that he wouldn’t mind playing to the crowd at a smaller event, either. “I have the feeling if you only play two or three Masters Series and you don’t play well in one, you come into the French Open maybe with not enough tennis,” Federer told a small group of reporters after his victory at the Masters Cup. “I like also going to smaller events and being the superstar. Even though I’m that everywhere I go, in small tournaments like Estoril I can enjoy it much more because it’s a smaller crowd, a smaller atmosphere; it’s nice to be able to share that.”

Back then, I put the odds at 50/50 that Federer, if his schedule demanded, would back out of Estoril this year, fearing that he might have too much tennis in his tired legs with more important events in Monte Carlo, which begins this week, and Rome coming up, not to mention the Olympics later in the year. Who would have predicted that not only would the folks in Estoril be thrilled to see Federer, but that Federer would need this tournament as much as it needed him?

Yesterday, at long last, Federer won his first tournament of the season after a week-long struggle that ended when Nikolay Davydenko retired with an apparent leg injury (Davydenko didn’t seem too troubled but decided he wouldn’t risk further injury, or waste energy, for Monte Carlo this week, a rather timid decision from the man who just won in Miami). Federer won the first set in a tie-break after saving set point. Davydenko led 2–1 in the second when he called it quits.

It’s encouraging for Federer to win this tournament, but not in this way and not with the way he played this week. It’s his first win since his decision to hire Jose Higueras, who has coached Jim Courier, Pete Sampras, Michael Chang, and Todd Martin, among others, as a part-time adviser (Federer and Higueras are calling the arrangement temporary, but seem headed toward a long-term part-time relationship like the one Federer had with Tony Roche until they parted ways last year). Federer’s tennis is still far from first-rate: He lost a set in his opening match to struggling Belgian Olivier Rochus and lost a 6–2 set in the semifinals to Denis Gremelmayr before recovering for a 2–6, 7–5, 6–1 victory. He continues to play shaky points, especially at tense moments.

There’s no point in looking for excuses. Weather conditions were not great in Estoril last week, but the weather applies to everyone. The fact that this was Federer’s first tournament on clay after two big events on hard courts wasn’t the problem, either. Much is made, every season, of the transition to clay — often (and wrongly) described as Federer’s “least favorite” surface — from hard courts. Everyone else on the tour has to make the same transition this time of year, and Federer is among the best equipped to do so. In the last three years, he has been the second-best player in the world on clay, which says a lot when the best player, Rafael Nadal, may one day be remembered as the best on the surface in the history of the game. There’s no excuse for Federer to have struggled at this event against far lesser players (Gremelmayr is ranked no. 104) other than the simple fact that he’s not playing well at the moment. There shouldn’t be any doubt that Federer will play exceedingly well at some point soon, but right now he’s yet to regain whatever his bout with mono took out of him physically and, more likely, mentally.

In Monte Carlo this week, Federer stands to make big gains in confidence if he can reach the final for the third straight year. His draw is a difficult one. His first match will likely be against Gilles Simon, a 23-year-old Frenchman with fast feet. From there, Federer could meet Fernando Verdasco, followed by Tommy Robredo or David Nalbandian in the quarterfinals, and perhaps Novak Djokovic in the semifinals. Nadal has kept Federer from winning the French Open for three consecutive years, but Djokovic could pose as much of a problem from this season on. The 20-year-old Serb played Nadal closer, in last year’s French Open semifinals, than Federer did in the final, even though Djokovic failed to win a set (Federer won one).

No player in the world has as much upside as Djokovic — he is far from his prime and could become much better as the year goes on. If he does, both Federer and Nadal will have their hands full. Djokovic might have the best game to defeat Nadal on clay, if only because his two-handed backhand is a better counterpoint to Nadal’s high-bouncing left-handed forehand than Federer’s at times shaky one-hander.

Nadal has set an astonishing pace for himself on clay. Since April 2005, he has played 94 matches on the surface. He’s lost only once, to Federer in Hamburg last year. He’s also never lost a match at the French Open. Such a streak has to end at some point, but will it be this year? We’ll see what happens in Monte Carlo this week.

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She took a fall and looked generally uncomfortable sliding (slipping, really) on the clay in Charleston, S.C., but Serena Williams won another tournament, this time against Vera Zvonareva, 6–4, 3–6, 6–3 at the Family Circle Cup. It was her first title on clay in six years. Williams, who defeated Maria Sharapova in the quarterfinals, has a record of 19–1. Zvonareva led by a break in the third set but double-faulted twice in a row late in the match to give Williams three chances at a 5–3 lead.

Mr. Perrotta is a senior editor at Tennis magazine. He can be reached at tperrotta@tennismagazine.com.