NEW YORK -- On only the fourth serve of his match with Lleyton Hewitt, Taylor Dent might have sensed that it wasn't to be his day.
Hewitt's backhand down the line was so wide it hit the top of the steel net post, which is moored close to the doubles line. But the ball caromed crazily back onto the court, over the head of a flummoxed Dent, who couldn't track it down. Two points later, Hewitt's backhand passing shot gave him the first break of the day and sent him on his way to a 5-0 lead.
But Dent didn't wither. He extended the No. 3 seed to an invigorating five sets and found himself two points from an ultimate tiebreak on four occasions. At the end, the Australian was just a little better, sliding a sneaky 114-mile-an-hour ace down the middle on his fourth match point.
Hewitt prevailed 6-3, 3-6, 6-7 (2), 6-2, 7-5.
And so, Dent's bid to join three American men in the U.S. Open's Round of 16 fell just short. On Monday, while the rest of America celebrates, Andre Agassi, James Blake and Robby Ginepri will all labor in an attempt to reach the quarterfinals. There were three U.S. men in the 2002 quarters, but they were named Agassi, Sampras and Roddick. This would represent a great leap for the next generation.
Agassi, the No. 7 seed, meets Xavier Malisse. Blake, who was ranked so low he needed a wild card into the tournament, plays No. 19 seed Tommy Robredo. It wouldn't be a shock to see both Americans advance. Ginepri was a 7-5, 6-7 (3), 6-4, 2-6, 6-3 winner over Tommy Haas late Saturday night. He takes on No. 13 seed Richard Gasquet, the 19-year-old Frenchman. Ginepri has as good a chance as anyone in his quarter of the draw, including No. 8 seed Guillermo Coria.
For Dent, who is in the midst of the best year of his 24-year-old life, this will rank as a massive disappointment. Hewitt, uncharacteristically shaky down the stretch, gave Dent numerous opportunities. The one that will haunt him -- an easy smash with Hewitt serving for the match at 6-5, 15-all. Inexplicably, Dent fired it into the net and lost an opportunity to take control of the game.
In a three-hour and 21-minute match that consisted of 318 points, that blown overhead was the most telling. Afterward, Dent dismissed that overhead and placed the blame on a familiar culprit: his serve. Hewitt broke it no fewer than eight times.
"It's disappointing, but it's actually more frustrating," Dent said. "I feel like I lost that match for the same reason that I've lost 99 percent of my matches for over the last year and a half or so. My serve just really let me down. It's a bit of a bummer.
"I kind of compare it to a junior -- you're working on forehands where the guy can hit a couple great, but a couple can hit the fence. It's just that inconsistent thing. Unfortunately for me, it's the most important shot I have to have for my game, and also the most stubborn shot, for whatever reason," he said.
Hewitt was the world's No. 1 player in 2001 and 2002 and has two Grand Slams on his resume, including the 2001 U.S. Open. Still, the Australian has had a quirky season. He had a cyst removed from his right foot in March and slipped on the stairs in his Sydney home in May, sustaining broken ribs. He missed the French Open, ending a streak of 25 consecutive majors played, but managed to reach the finals in the Australian Open and the semifinals at Wimbledon
"I felt like there was a lot of areas of my game that weren't quite clicking today," Hewitt said. "It was more a matter of trying to find a way to win today and get in the locker room and look forward to the next round."
Hewitt is a classic baseline player, who will readily come to net when an obvious opportunity presents itself. For Dent, every point is an opportunity to come to net. He is a rare serve-and-volley player, one of only a handful on the ATP. It's in his blood; father Phil Dent, an Australian, was a serve-and-volleyer, and so was his mother, American Betty Ann Stuart.
Hewitt won the first three matches between the two, but Dent broke through in, of all places, Adelaide, Australia, the place where Hewitt was born. Dent won in straight sets in early January and took some confidence from it. Six months later, on the grass at Wimbledon, Hewitt beat Dent in four sets.
Dent was broken in his first two service games and then rallied to hold serve 10 times in a row. He won the second set when, serving at 5-4, he earned seven set points and converted the last one when Hewitt dumped a well-angled serve into the net.
In the first game of the third set, Hewitt fell into a love-40 hole and managed to escape. With Dent serving at 4-3 and 5-4, Hewitt, almost inexplicably, broke him. Serving at 5-6, Dent saved two set points and forced a breaker. After running out to a 5-0 lead, Dent won it when Hewitt's backhand sailed long.
Hewitt's calling cards, though, are toughness and resilience. After simmering on his changeover chair, he came out and broke Dent in the first game of the fourth set and rolled the rest of the way.
The fifth set was an electric affair, with both players showing considerable nerves. Hewitt broke Dent in the 11th game on the strength of a forehand service return winner, a terrific scrambling point that ended with a netted dent overhead, a double fault and swinging forehand volley. Thus, it came down to the 12th and final game and Hewitt found a way, as he often does, to win.
Greg Garber is a senior writer for ESPN.com.