By Richard Pagliaro, Tennis.com

Lining another flat forehand into the net, Serena Williams shoved the air in disgust, as if admonishing a dance partner for repeatedly stepping on her toes. The fifth-seeded American looked out of step and out of sorts, fighting both herself and an inspired Virginie Razzano. Williams would win neither battle.

The 111th-ranked Frenchwoman rallied from a 1-5 deficit in the second-set tiebreaker, rolled to a 5-0 lead in the third set, then fought off a late Serena surge, converting her eighth match point to seal a shocking 4-6, 7-6 (5) 6-3 upset that spanned three hours, three minutes and sent French fans into a frenzy.

It was, by far, Razzano's biggest Grand Slam win, and it was Serena's first Grand Slam opening-round loss. The 2002 French Open champion was 46-0 in the first round of majors and undefeated on clay this year, but never really found her range or rhythm in an erratic effort. Serena careened from tight, tentative shots that sometimes landed in the middle of the court to impulsive, overly-ambitious blasts that sailed beyond the baseline. One of the best closers of the Open era gagged near the finish line today and choked back tears after losing six straight straight points in the second-set tiebreaker.

Credit Razzano for her resilience in playing through apparent calf cramps that caused her to squeal in pain during a few points, eliciting a point penalty for hindrance in the third set. When Williams' backhand landed long on the eighth match point, Razzano had cause for screaming celebration.

It was a particularly poignant moment for the 29-year-old crowd favorite, whose fiancé and former coach, Stephane Vidal, died of a a brain tumor eight days before her first-round match at last year's French Open. Wearing a black ribbon on her shirt and pain etched on her face, Razzano faced what she called "a mission impossible" in a somber first-round loss. Today, she played with passion and poise in pulling off an improbable comeback.

This was an adventure of a match with wild momentum shifts. Signs of stress were clear as Serena lost her first two service games before rallying to take the 46-minute first set on a Razzano double fault.

Williams crunched a forehand winner to seize a seemingly commanding 5-1 lead in the second-set tiebreaker—then she made a major mess of things. Serving at 5-2, Williams slammed a biting serve that a lunging Razzano blocked back. Williams, already mentally counting the point, did not play the return, assuming it would stray long. Instead, it landed on the line. At 5-3, Williams belted a backhand winner down the line that would have given her match point, but the linesman made a late call on the prior shot, prompting a replay, which Razzano won. By the time the red dust settled, Razzano reeled off six straight points and danced to a bathroom break at 7:59 p.m. Paris time with the match deadlocked. A dazed-looking Serena then completely disinegrated, as Razzano stormed out to a 5-0 lead.

Digging down to summon her competitive spirit, Williams found the line with a forehand return, broke for 2-5, then held at 15 for 3-5. The marathon, 23-minute, 12-deuce final game was a microcosm of the match, with spirited rallies and paralyzing nerves on display. On the fifth match point, Williams whipped a stunning backhand winner down the line that singed the sideline, prompting a collective groan from the fans. It seemed that shot might rouse her, but on this day Razzano would not be denied.

Razzano erupted in a wide smile when Williams' backhand sailed long on match point number eight; the woman who called the death of her fiance "permanent pain" created pure joy in her Paris return.

Loading Slideshow...
  • Serena Williams Upset

    Serena Williams of the US returns in her first round match against Virginie Razzano od France at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012. Razzano won in three sets, 6-4, 6-7. 3-6.

  • Serena Williams Upset

  • Serena Williams Upset

    Virginie Razzano of France returns in her first round match against Serena Williams of the U.S. at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012. Razzano won the match in three sets 6-4, 6-7, 3-6.

  • Serena Williams Upset

    USA's Serena Williams reacts as she plays France's Virginie Razzano during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    USA's Serena Williams reacts as she plays France's Virginie Razzano during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    USA's Serena Williams reacts as she plays France's Virginie Razzano during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    France's Virginie Razzano clenches her fist as she plays USA's Serena Williams during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    USA's Serena Williams runs to the ball as she plays France's Virginie Razzano during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    USA's Serena Williams returns the ball to France's Virginie Razzano during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    France's Virginie Razzano backhands to USA's Serena Williams during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    USA's Serena Williams sits during a break as she plays France's Virginie Razzano during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    USA's Serena Williams returns the ball to France's Virginie Razzano during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    USA's Serena Williams reacts as she plays France's Virginie Razzano during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    Virginie Razzano of France returns in her first round match against Serena Williams of the U.S. at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012.

  • Serena Williams Upset

    Serena Williams of the U.S. returns in her first round match against Virginie Razzano of France at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012.

  • Serena Williams Upset

    Virginie Razzano of France celebrates defeating Serena Williams of the U.S. in the first round match at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012. Razzano won in three sets, 6-4, 6-7. 3-6.

  • Serena Williams Upset By Samantha Stosur 6-2, 6-3 In US Open Final

    Serena Williams of the U.S. rserves in her first round match against Virginie Razzano of France at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012.

  • Serena Williams Upset

    Serena Williams of the U.S. returns in her first round match against Virginie Razzano of France at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012.

  • Serena Williams Upset By Samantha Stosur 6-2, 6-3 In US Open Final

  • Serena Williams Upset

    Serena Williams of the US gestures in her first round match against Virginie Razzano od France at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012. Razzano won in three sets, 6-4, 6-7. 3-6.

  • Serena Williams Upset

    France's Virginie Razzano, left, shakes hands with USA's Serena Williams after their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    France's Virginie Razzano rests on her chair after defeating USA's Serena Williams during their first round match in the French Open tennis tournament at the Roland Garros stadium in Paris, Tuesday, May 29, 2012.

  • Serena Williams Upset

    Serena Williams of the US listens to a question of a reporter during a press conference after losing her first round match against Virginie Razzano of France at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012. Razzano won in three sets, 6-4, 6-7. 3-6.

  • Serena Williams Upset

    Serena Williams of the US listens to a question of a reporter during a press conference after losing her first round match against Virginie Razzano of France at the French Open tennis tournament in Roland Garros stadium in Paris, Tuesday May 29, 2012. Razzano won in three sets, 6-4, 6-7. 3-6.