Britain's Katie O'Brien, Naomi Cavaday and British number one Anne Keothavong all lost in round one at Wimbledon.
O'Brien lost in the first round in both 2004 and 2005
O'Brien missed out on a second round tie with Martina Hingis after losing 2-6 7-6 (7-2) 6-2 to Tathiana Garbin despite leading by a set and 3-1.
Meanwhile, Cavaday pushed 18th seed Ai Sugiyama hard in her rain-interrupted before falling to a 6-4 7-5 defeat.
Keothavong offered least resistance - slipping to a 6-0 6-2 defeat at the hands of Karolina Sprem.
O'Brien had seemed on course for the first Wimbledon victory of her career after winning an error-strewn first set and going a break up in the second.
But Garbin hit back to level at 4-4 and eventually force a tie-break which she won to level the match.
And the Italian stepped up her game in the final set to end O'Brien's hopes.
Katie O'Brien was furious with herself after losing the lead having been two points away from victory at 5-4 in the second set.
"There were points I could have won. It was definitely a winnable game and if I could go back and play those points again....
"I was a bit anxious in the third set and if I had been a bit calmer it could have been different.
"The stakes were so high and it will take a while to get over it."
Cavaday resumed 5-4 behind after rain brought a premature end to play on Monday and the 17-year-old quickly lost the first set to Sugiyama but she put up stiff resistance in the second.
Cavaday opened up a 4-1 lead to raise the British crowd's hopes, but allowed Sugiyama back into the match.
And, given the opportunity, the veteran Sugiyama sealed the win efficiently.
Cavaday was ranked nearly 500 places below her opponent
Cavaday had found herself 0-4 down in the first but then settled and had played her way back to 4-5 when rain forced the players off court.
Sugiyama successfully served for the first set on the resumption.
Cavaday, ranked 514 in the world, came through last week's wildcard play-offs to earn her place at Wimbledon.
Sugiyama has been ranked as high as eighth in the world and reached the quarter-finals at Wimbledon two years ago.