Four-time champion Andy Roddick crashed out of the Wimbledon warm-up event at Queen's Club on Wednesday as France's Edouard Roger-Vasselin clinched a shock 6-4, 4-6, 7-5 victory over the seventh seed.
Roddick has slipped out of the top 30 in the world rankings after an injury-ravaged campaign, but losing to Roger-Vasselin, ranked 67th, on the grass he regards as his favourite surface is a new low for the American.
It was the 29-year-old's 11th defeat in 18 matches this year and raises doubts about his ability to mount a strong challenge at Wimbledon, where he has reached the final three times.
Roddick's body is showing signs of wear and tear after over 10 gruelling years on the ATP Tour and he has struggled with ankle and hamstring injuries this year.
After a dispiriting first round exit against Nicolas Mahut at the French Open recently, Roddick had hoped the grass courts would revitalise his season.
Instead it looks like going from bad to worse for the former world number one.
Such is Roddick's frustation at his travails, he even hinted recently this year's Wimbledon could be his last appearance at the All England Club.
That would have been unthinkable three years ago when he came within touching distance of beating Roger Federer in an epic Wimbledon final.
Now it seems entirely possible. The American has always thrived on the lush lawns of west London, but his 12th visit to Queen's won't live long in his memory.
After losing the first set, Roddick hit back to get the only break of a hard-fought second set.
But the former US Open champion couldn't convert a match point at 5-4 in the final set and Roger-Vasselin made him pay as he broke for a 6-5 lead before serving out a shock win.
Roddick wasn't the only seed to fall in the second round as Taiwan's Lu Yen-Hsun held his nerve to win a tie-break battle with 16th seed Ivo Karlovic.
Lu, ranked 57th in the world, came from a set down to defeat Igor Kunitsyn in the first round and he repeated the feat to record a 6-7 (3/7), 7-6 (8/6), 7-6 (9/7) victory over Croatia's Karlovic.
After winning the Singapore Challenger event earlier this year and reaching the third round at the Australian Open, Lu has climbed from 82nd in the world at the start of the year to just outside the top 50.
He continued in that vein here. Although Lu lost the first set, he matched the big-serving Karlovic blow for blow to take the second set on a tie-break.
The final set went to a tie-break as well and it was 28-year-old Lu who took it to clinch a third round meeting with Janko Tipsaveric or Ryan Sweeting.
Italy's Simone Bolelli also claimed an impressive scalp as he defeated French fourth seed Gilles Simon 4-6, 6-3, 7-6 (7/2).
Bolelli is ranked 107 places below Simon, but the 26-year-old made a mockery of that gap as he showed great poise and determination to bounce back from a slow start against the world number 13.
Sixth seed Marin Cilic wasted little time booking his place in the third round as the Croatian demolished Australia's Matthew Ebden 6-2, 6-1 in just over an hour.
Japan's Tatsuma Ito reached the second round with a rain-delayed 7-6 (8/6), 4-6, 6-2 win over Italy's Paolo Lorenzi.