Germany's Tommy Haas upset world number one Roger Federer at the invitational Kooyong Classic in Melbourne on Wednesday, ending the Swiss player's chances of defending the title.
Federer was beaten 3-6, 6-4, 6-4. World number three Andy Roddick kept his chances alive, however, with a comfortable 6-2, 6-2 victory over French teenager Gaels Monfil.
Under the Australian Open warm-up tournament's format, all of the first day's losing players drop down to play off for fifth to eighth, while the day's winners will play for first to fourth.
The 26-year-old Haas broke Federer twice in the third set and served out the final game to run out a winner under overcast skies and cool temperatures in suburban Melbourne.
SPECTACULAR SHOTS
Federer appeared to struggle with his timing, hitting several forehands either long or wide, while Haas scrambled for nearly every point, often producing spectacular running passing shots.
"I didn't think I played that badly. I played a pretty good first set," Federer told reporters.
"I struggled for rhythm in the beginning in the first six games or so, but then I broke him twice and won the set and I think he was struggling early on.
"I think he played good after that. He hardly missed a ball and served consistently and made it hard for me.
"I think my last couple of years my first round at Kooyong have always been a struggle and it's always close. I usually have a three-setter but this time I lost."
Haas, who has beaten Federer each of the three times they have met in Australia, said the victory would help him heading into next week's Australian Open.
"I'm very happy with the game," said Haas. "This is definitely a good victory, not only for my own confidence but the game and gives me good hopes to play next week."
The eight-player tournament is one of the traditional warm-up events for the Australian Open starting in Melbourne on Monday.