Britain's representation in the second round at Wimbledon suffered a triple blow as Anne Keothavong, James Ward and Elena Baltacha failed to progress.
Keothavong's bid for a first appearance in the third round was ended as Italy's Sara Errani beat her 6-1 6-1.
British women's number two Baltacha was well beaten 6-0 6-4 in 71 minutes by defending champion Petra Kvitova.
Andy Murray is now the sole home hope in the men's draw after Ward's 6-3 5-7 6-4 6-7 (3-7) 6-3 loss to Mardy Fish.
"I stayed in there as much as possible," said 25-year-old Londoner Ward, who saved match point to take the game to a deciding fifth set before losing after more than four hours of play.
"He was playing well but I gave it my all and it just wasn't good enough. It might not have been the best match of my career because I lost but the atmosphere was great and the standing ovation at the end was unbelievable."
Not many gave much hope to Ward - whose best result came when he beat then world number 14 Stanislas Wawrinka on his way to the semi-finals of Queen's in 2011 - even though Fish was competing for the first time since a procedure to correct a heart problem.
Tenth seed Fish comfortably won the first set and seemed on course for a straightforward victory when he conjured three break points in the 10th game of the second set.
But the nerveless Ward served his way out of trouble and levelled the match by breaking Fish with a delicious forehand winner.
Fish, ranked 161 places above his opponent, again seemed in control after securing the third set and breaking Ward early in the penultimate set. The wildcard refused to surrender, however, saving match point before breaking back and winning the fourth set tie-break.
It was an effort that had the partisan crowd on their feet, but Ward could not maintain such standards and netted a simple forehand in the eighth game of the decider, allowing the American to serve for the match.
Ward's marathon match meant Baltacha was moved to Court Two to face fourth seed Kvitova, who mercilessly dispatched the 28-year-old with some powerful groundstrokes.
British number one Keothavong, seeking a career-best performance at her home Grand Slam, appeared nervous before a patriotic crowd on a sunny Court Two.
The occasion seemed initially to overwhelm the British number one as she was broken with ease by the French Open finalist in the first game.
The 28-year-old, one of four Britons hoping to progress on day four, later admitted she "forced play too much" during the 61-minute defeat.
"To lose in that fashion, it's not particularly pleasing. I managed to kind of just hit myself off the court, I guess," said the Londoner.
Errani's deft drop shots troubled Keothavong, while her faltering serve - overall she won only 59% of points on her first serve and 12% on her second - gave the diminutive Errani plenty of opportunities.
Although Errani was not playing on her favourite surface, the 25-year-old was varying play nicely, treating spectators to an array of lobs and irretrievable volleys, and broke in the fourth and sixth games of the second set to secure a comfortable win and a third-round tie with either Yaroslava Shvedova or Kiki Bertens.
There was further disappointment for British tennis fans as Heather Watson and Laura Robson, selected for the Olympics doubles team, lost 6-3 7-6 (7-4) to Su-Wei Hsieh and Sabine Lisicki.
But Robson's fortunes improved later in the day as she and mixed doubles partner Dominic Inglot beat Scott Lipsky and Natalie Grandin 7-6 (7-2) 7-6.
JohannaKonta and Naomi Broady were beaten 6-2 6-4 by third seeds Kveta Peschke and Katarina Srebotnick in the ladies' doubles, while Oliver Golding and Liam Broady lost in the men's doubles, falling 7-6 (7-2) 4-6 6-3 6-4 to 12th seeds Santiago Gonalez and Christopher Kas.