Shanghai: American fifth seed Mardy Fish was upset by Australian teenager Bernard Tomic 4-6, 6-1, 6-4 on Tuesday in the second round of the Shanghai Masters.
The 18-year-old Tomic broke the ninth-ranked American twice to win the second set in 31 minutes. Fish fought off three more break points in the third set before Tomic was converted on his fourth chance to go up 5-4.
The result hurts Fish's chance of qualifying for the season-ending ATP World Tour Finals in London.
Americans Andy Roddick, Ryan Harrison and Alex Bogomolov Jr. advanced. Roddick edged 20-year-old Grigor Dimitrov of Bulgaria 7-6 (3), 7-5. The 10th-seeded American fought off a set point in the second set to advance to the third round.
The 19-year-old qualifier Harrison beat 11th-seeded Viktor Troicki 6-3, 6-3, while Bogomolov Jr. defeated Marcel Granollers of Spain 6-2, 6-3.
Stanislas Wawrinka stopped Donald Young of the United States 6-7 (5), 7-6 (2), 6-2.
Tomic, who lost to Fish in the quarter-finals of the Japan Open last week, is having a break-out season. He reached the quarter-finals of Wimbledon and cracked the top 50 in the rankings this week at No. 49.
"I can't expect much more for myself. I've had a good last six months. I'm playing well here," he said. "I think you just gotta play tennis, have fun. That's what I realized, not to have a lot of pressure."
Roddick came back from a break down in the second set to tie 4-4 when the big-hitting Dimitrov put a backhand into the net after slipping at the end of a 43-stroke rally.
The Bulgarian broke back in the next game, prompting an angry Roddick to slam his racket into his tennis bag during the changeover.
"I don't know that I made a first serve that game, so that was frustrating for me," Roddick said. "I felt like I was returning pretty well and hitting my forehand pretty well. Then all of a sudden, you know, I'm not putting a first serve in the court. So I was kind of annoyed. I felt like I was going backwards."
"The guy doubles three times and lets you back in, then you donate it right back. That's not a recipe to win a match. But I got through it. I do that pretty well - get through matches when everything isn't going perfectly."
Roddick saved a set point on Dimitrov's serve before breaking his opponent at love to close out the match.
"He's definitely got all the shots," Roddick said. "He should have closed me out in the second set."
Dimitrov finished with 28 winners, nearly twice as many as Roddick, but also had 51 unforced errors.
Roddick will play seventh-seeded Nicolas Almagro of Spain, who defeated countryman Tommy Robredo, 7-5, 6-3.
Almagro, who has won three titles this year, is trying to clinch one of the four remaining spots at the ATP World Tour Finals.
The only other seeded players to fall Tuesday were two Serbs — 11th-seeded Troicki and ninth-seeded Janko Tipsarevic.
Tipsarevic lost to Feliciano Lopez 7-6 (2), 7-6 (3), his second straight first-round defeat after capturing his first ATP title in Kuala Lumpur last month.
German Florian Mayer, seeded 15th, knocked out David Nalbandian, 6-3, 6-4. Nalbandian, a former Wimbledon finalist, has struggled since returning from a hamstring injury this summer.
Other winners included Milos Raonic, who came back to defeat Michael Llodra of France, 6-7 (2), 6-2, 7-6 (5), as well as eighth-seeded Gilles Simon, 12th-seeded Alexandr Dolgopolov of Ukraine and 14th-seeded Jurgen Melzer of Austria.
First seed Rafa Nadal and Britain's world number four Andy Murray, who beat the Spaniard in the Japan final last Sunday, play their first matches on Wednesday. Novak Djokovic and Roger Federer pulled out of the week-long tournament.
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