- Greg Garber, Writer, Reporter
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NEW YORK -- Many of the men's top seeds have struggled in the heavy, early going of the U.S. Open. So why should Andy Roddick be any different?
But while Novak Djokovic, Robin Soderling, Fernando Verdasco and David Nalbandian all went the full legal limit -- and survived -- Roddick joined Lleyton Hewitt and Marcos Baghdatis as a surprising victims Thursday night.
Roddick, the 2003 champion here and former No. 1, was sluggish and defensive -- perhaps the lingering aftermath of a mild case of mononucleosis that struck him earlier this summer -- falling 3-6, 7-5, 6-3, 7-6 (4) in Arthur Ashe Stadium.
"I feel fine," Roddick said after the match. "I feel like I am going to get some rest tomorrow."
Make no mistake though, Tipsarevic, a bearded 26-year-old from Serbia who wears sleek industrial art glasses and sports a Dostoyevsky tattoo, played beautifully. On this night, a journeyman tennis player, who makes a nice living inside the top 100, pulled off the upset of the tournament so far.
"He played great tonight," Roddick said. "You know he's going to take big swings and pot shots at the ball. I thought he played very high-risk and executed for four sets. I kept telling myself, 'This has to have an expiration date on it.' Unfortunately, I needed another set for that.
It was the second-most embarrassing exit here for the No. 9 seed, after Gilles Muller's first-round upset 2005.
Tipsarevic, who missed three weeks before the tournament with an injured ankle, stroked 66 winners -- 26 more than Roddick -- and won 81 percent of his first-serve points with zero double faults. Afterward, he was calm, almost laconic.
"Of course, I made a couple of unbelievable shots from back of the court, but most of the winners that I made I was stepping and being close to the line," said Tipsarevic. "That's the point on the court where I'm most dangerous."
Roddick dropped only seven games in his first-round match -- on his 28th birthday -- but later admitted that his physical condition was something less than 100 percent. He declined to give a specific number and said he would not discuss the topic further.
It's been a mixed bag for Roddick this summer, but some wondered if the return to the scene of his only Grand Slam singles title might stoke a fire. Instead, he often played passively, making a wide variety of tactical errors, at least in the eyes of the McEnroe brothers, John and Patrick, who were in the broadcast booth. Numerous times, Roddick was in position to be aggressive and failed to step forward.
For example: On set point in the third, Roddick was near the service line, in a position to make a winning forehand volley on Tipsarevic's lunging backhand down the line. Roddick made a move as if to hit the ball, but pulled off -- and it easily landed inside the court.
In short, he looked tired.
On three occasions, he was called for literally dragging his feet -- on the baseline. The first one set him off and seemed to bring some passion to the surface.
Last year, the enduring moment of this tournament was created when Serena Williams was called for a foot fault on the penultimate point of her match with Kim Clijsters. Because of an earlier warning, a point was awarded to Clijsters, who walked off as the winner. Eventually, she became champion.
Roddick was serving at 2-5 in the third set with the match square, when he was called for a foot fault. Replays showed the call was an accurate one, but Roddick nearly lost his mind. He was still fuming when Tipsarevic took the set -- and a daunting lead.
"I have to change my shorts," Roddick said as he stalked past chair umpire Enrick Molina. "That's ridiculous."
Roddick managed to force a fourth-set tiebreaker, but Tipsarevic simply played better. Roddick closed it to 4-5, but Tipsarevic blasted an unreturnable serve and then boldly worked his way to net and knocked off one last backhand volley.
Meeting Roddick at net, Tipsarevic was so moved he nearly buried his head in Roddick's chest.
"I just said, 'The last time you beat me in a Grand Slam second round, you lost the last match, so don't do that,' to which he head-butted me, which was fun," Roddick related."
Given Roddick's evasiveness regarding his physical condition and the history he shares with the thoughtful Serb, maybe this shouldn't have come as a surprise. Although Roddick won their first meeting, at Wimbledon in 2006, Tipsarevic returned the favor two years ago at the All England Club. He beat Roddick, a three-time finalist there, in the second round.
And now he's done it again.
"I'll sleep a lot better than I did at Wimbledon, which basically felt like I handed someone a win," Roddick said. "Tonight, I felt like the guy earned it. That's probably easier to deal with when he comes up with the goods."
Said Tipsarevic: "In Wimbledon, when I won, I felt that I was lucky and that Andy choked on important moments. But here, I feel it was a different story. "
In retrospect, this may be seen as a telling moment, a paradigm shift in American tennis. On the day that 18-year-old Ryan Harrison won his first match -- and was joined by emerging players Sam Querrey and John Isner in the second round -- Roddick looked old and tired.
Greg Garber is a senior writer for ESPN.com.