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Andre Agassi, who had confirmed his retirement plans prior to the tournament, lost to German qualifier Benjamin Becker 7-5, 6-7 (4), 6-4, 7-5 in an emotional day that saw the 36-year-old break down after the match.
In front of his family and friends, Agassi was saluted by the sold-out New York crowd as they chanted his name for several minutes.
Worn down and wincing in pain from a back injury, Agassi couldn't handle the power thrown at him by Becker, who is ranked 112th in the world.
Becker fired 27 aces and fittingly ended the match with a blistering serve down the line. In a career filled with brilliant moments, Agassi won all four Grand Slam events and finished with eight titles in total.
"The scoreboard shows that I lost today," a weeping Agassi told the crowd. "But what the scoreboard doesn't show is what I feel."
Becker, who needed to win three qualifying matches to simply advance to the U.S. Open, praised Agassi for his stellar career.
Agassi's wife, tennis legend Steffi Graf, and their two young children looked on.
"He was my idol growing up," the 25-year-old Becker said.
The tournament also ended on a painful note for Agassi, who received cortisone and anti-inflammatory shots to keep playing this week.
Rest didn't help
Even with an extra day of rest after a rain delay Saturday, Agassi appeared timid from the very first game.
But after double-faulting to give the first set to Becker, Agassi bounced back to win the second in a tiebreaker.
After Becker won the third set, the German cramped up in the fourth, only competing on his serves. However, with the score tied 5-5, Becker came alive to break Agassi before closing out the match on his serve.
The crowd was clearly on Agassi's side, booing his opponent whenever he would make a drop shot that forced the American to run.
Prior to his agonizing, five-set victory over Marcos Baghdatis, Agassi said he envisioned the ending and how he didn't want to finish his career.
"I just don't want to go off the court limping," he said. "It's not what I want to do."
Agassi finished his career with a match record of 870-274.
Becker next plays No. 9 Andy Roddick, who defeated Fernando Verdasco 6-7, 6-3, 6-4, 6-7, 6-2.
Two-time defending champion and world No. 1 Roger Federer easily dimissed American Vince Spadea 6-3, 6-3, 6-0 in the evening session. Federer next meets Marc Gicquel, who eliminated 2004 French Open champion Gaston Gaudio 6-0, 4-6, 4-6, 6-1, 7-6
In other men's action, the 2002 U.S. Open champion Russian Marat Safin of Russia upset No. 4 seed David Nalbandian of Argentina, 6-3, 7-5, 2-6, 3-6, 7-6 (6)
The match with Nalbandian and Safin was one of two matches still in the second round because of Saturday's rain delay.
Safin, who has battled injuries in recent months, won the 2002 U.S. Open.
No. 2 seed Rafael Nadal of Spain defeated South Africa's Wesley Moodie, 6-4, 7-6, 7-6.
Spaniard Tommy Robredo, the No. 6 seed, advanced to the fourth round after beating Stanislas Wawrinka of Switzerland, 6-3, 6-4, 6-2.
No. 5 James Blake beat 1998 French Open champion Carlos Moya 6-4, 7-6, 2-6, 6-3.
Former champion and No. 15 seed Lleyton Hewitt of Australia also advanced with a 6-3, 6-1, 6-2 win over No. 20 Novak Djokovic of Serbia.
On the women's side, top seed Amelie Mauresmo of France needed three sets to defeat Italian Mara Santangelo in the evening session.
No. 3 Maria Sharapova defeated Elena Likhovtseva 6-3, 6-2, and No. 10 Lindsay Davenport of the U.S. saved two match points before beating Slovenian Katarina Srebotnik, 3-6, 6-3, 7-6.
Also advancing were No. 7 Patty Schnyder of Switzerland and No. 12 Dinara Safina of Russia.
Unseeded Serena Williams defeated No. 16 Ana Ivanovic 6-2, 6-4.
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I always liked her as a tennis player - she's had a great career thus far. It's rumoured this is her last US Open, and she has a good chance of winning it, and it'd be great to see her go out on top.
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...I heart him (esp. the days when him and Sempras battled it out @ Wimbledon) 
