Michael Phelps finished fifth in the 200-meter butterfly Saturday at a short-course World Cup meet that featured six world records.
Nikolay Skvortsov of Russia, who had the fastest qualifying time, won the final in 1:50.58. Phelps squeezed in as the eighth and last qualifier in the heats.
The American star, who won eight gold medals at last year's Beijing Olympics, finished in 1 minute, 52.26 seconds in the final. Phelps is competing in an old-style swimsuit that will become the standard on Jan. 1.
Phelps has yet to win a race on his European tour. He failed to make three finals at another World Cup meet in Stockholm this week. He was second in the 200-meter medley in Sweden.
He had been entered in the 100 medley in Berlin but skipped the race Saturday because the heat was shortly after the 200 butterfly qualifying.
On the eve of the Berlin meet, Phelps said he was not in the best of shape, apart from the disadvantage of not swimming in one of the high-tech swimsuits. Phelps left the pool Saturday without speaking to reporters.
While Phelps continues to struggle, German rival Paul Biedermann bounced back from an injury to shatter the 400-meter freestyle world record.
Biedermann won in 3:32.77 to slash nearly 2 seconds off the old mark of 3:34:58 set by Grant Hackett of Australia on July 18, 2002, in Sydney.
Biedermann defeated Phelps in the 200 freestyle and broke the American's world record to win the gold medal at the world championships in Rome in August. They will swim against each other in the same event Sunday.
"I was more excited today than at the world championships, because I didn't really know what was possible for me because of my injury," said Biedermann, who tore a muscle in his left thigh and had to skip the Stockholm meet. "Without the high-tech suits, it will be difficult to improve this record in the future.
"Tomorrow's 200 freestyle will surely be an interesting race," Biedermann said.
Phelps has promised to race as hard as he can in the 200 free, although he's seeking his form after taking time off following the worlds.
Biedermann's coach did not expect a classic showdown between his swimmer and Phelps.
"We surely won't see a great duel," coach Frank Embacher said.
The first day of the weekend meet produced a flurry of world records. Shiho Sakai of Japan broke the women's 200 backstroke by finishing in 2:00.18.
"I still can't believe it," the Japanese swimmer said. "It's a pity I didn't break 2 minutes, but that's my goal for the future."
Also, Steffen Deibler of Germany improved his own 50 butterfly mark to 21.80; Cameron van der Burgh of South Africa improved the 50 breaststroke record to 25.25; and Leisel Jones of Australia broke her own 100 breaststroke mark with a time of 1:03.30.
Jones, the Olympic champion in the event, skipped the world championships after nine years on the Australian team.
"I am now really relaxed and enjoying myself," Jones said, adding that she was looking to become the first Australian swimmer to compete in four Olympics at the 2012 London Games.
Sergey Fesikov of broke the 100 medley record in 50.95 in the heats and then won the final in 50.96.