British trio Andy Murray, Greg Rusedski and Tim Henman all went out of the Cincinnati Masters on Wednesday.
Teenager Murray battled gamely against an erratic Marat Safin before losing his momentum in a 4-6 6-1 1-6 defeat to the Russian fourth seed.
Rusedski got off to the perfect start against third-seeded Lleyton Hewitt before he too faltered, eventually falling 1-6 7-5 6-4 to the Australian.
And an out-of-form Henman slumped to a 6-4 6-4 defeat to Juan Ignacio Chela.
Henman, the British number one, has won just one match since Wimbledon and is desperately seeking form ahead of the US Open.
In the first set of his match, Murray was broken in his first game but rallied to break back in the sixth only to lose his serve again.
He pluckily saved two set points in the ninth game on his own serve but that merely delayed the inevitable as the big serving Russian prevailed 6-4.
The young Scot came back with a vengeance in the second set as he flew through to lead 5-0 before taking it in a dominant fashion.
But Safin showed ruthlessness in the decider to book a place in the third round against Dominik Hrbaty or Robin Soderling.
Hewitt, meanwhile, was almost unrecognisable in the first set against Rusedski, making countless unforced errors and winning only 11 points.
But the Australian gradually found his rhythm and broke serve for the first time at 6-5 to level the match.
Rusedski had been in devastating form on serve but he faltered at the crucial moment, double-faulting on Hewitt's first match point.
Hewitt admitted he was surprised by Rusedski's level of play.
"He served extremely well," said Hewitt.
"He didn't give as many cheap points as he maybe normally does, especially from the back and on my service games.
"I tried to make him play more as the match went on. The best thing about the match today is that I get a crack at someone tomorrow."
It was a bitter blow for Rusedski, who has been in brilliant form over the North American hardcourt season.
Defeat to Hewitt was only his fourth in 18 matches since losing in round two at Wimbledon.
And the British number two may be wondering how he is not celebrating a fourth career win over Hewitt.
In the second set, the 31-year-old had a break point at 1-1 and later netted a simple backhand which would have given him a 3-2 lead on serve.
Hewitt saw off two more break points at 4-4 and grew in confidence after snatching the second set against the odds.
The Australian goes on to face Croatian Mario Ancic, who upset 16th seed Richard Gasquet of France 6-4 7-6 (8-6).
Rusedski consoled himself from his exit with the possibility of being seeded at the US Open.
Rusedski said: "I should get a seeding at the Open unless two or three people have a phenomenal week.
"It's always nice to get seeded at a major. It means you miss Federer and Hewitt and Roddick in the first round.
"I might actually get a decent draw at a Grand Slam for once now. It's been a few years."