updated 3:19 p.m. ET June 26, 2008

WIMBLEDON, England - Former two-time Wimbledon finalist Andy Roddick didn't even get to the third round this year.

Roddick, who lost in the 2004 and 2005 Wimbledon finals to Roger Federer, went out 6-7 (5), 7-5, 6-4, 7-6 (4) on Thursday to 40th-ranked Janko Tipsarevic of Serbia, who has never gone past the fourth round at a major.

The sixth-seeded Roddick went 0-8 on break points, while Tipsarevic converted both of his break chances. Roddick had three set points in the fourth set but couldn’t capitalize, and Tipsarevic finished him off in the tiebreaker, falling to his hands and knees in celebration on Centre Court.

“This means the world to me,” Tipsarevic said.

He pulled off the biggest win of his career just a day after No. 3-ranked countryman Novak Djokovic was knocked out on the same court by Marat Safin.

“I’m just glad that I won and Serbia will have more representatives in the men’s singles draw,” Tipsarevic said.

Nadal, a two-time Wimbledon runner-up who swept to his fourth straight French Open title without dropping a set, lost the first set against the talented Gulbis — a quarterfinalist at the French — when he was broken in the 12th game.

But Nadal sailed through the next set, took the third in a tiebreaker and got the decisive break for 5-3 in the fourth.

No. 9 James Blake — who has never gone past the third round at Wimbledon — lost to Germany’s Rainer Schuettler, 6-3, 6-7 (8), 4-6, 6-4, 6-4 and No. 12 Andy Murray had a 6-4, 6-2, 6-2 win over Belgium’s Xavier Malisse.

MORE FROM TENNIS

Tennis Section Front

2 arrested for stalking Indian tennis star Mirza Tennis and tweeting for Gimelstob Blake to play 6-foot-10 Karlovic in Davis Cup Safin dropped from singles matchup with Israel Two-time defending Newport champ Santoro wins Tennis player suspended, fined for racial abuse Dulko saves more match points to make Bastad semis   Video: Venus gives back to kids   Video: 4-year-old phenom dazzles tennis world Interactive: Building the perfect tennis player Tennis Section Front   Add Tennis headlines to your news reader: