Laura Robson, Heather Watson and Naomi Broady lost their first round matches at the Nottingham Open but Tara Moore moved into the second round.
After British number one Johanna Konta set the ball rolling with victory on Monday over American Victoria Duval, it was the turn of the three women immediately behind her in the British rankings and the recovering Robson to take centre stage.
Robson, given a wildcard into this week's grass-court event as she continues he return after a long-term absence following two rounds of wrist surgery, was up against Michelle Larcher de Brito, ranked 62 places above her.
Robson, who has won only one WTA tour match and followed a first-round exit last week's in Eastbourne on the ITF Tour with another defeat despite some encouraging signs.
Portugal's world number 246 Larcher de Brito took the opening set 6-3 before a fightback from 22-year-old Robson put her into a 4-1 lead in the second, but her opponent reeled off five games in succession to move to the brink of victory.
Robson broke at 4-5 to give herself hope taking the match to a decider but Larcher de Brito stayed strong to claim the next two games and a place in the second round
British number two Watson is seeded sixth and looked to be heading for a straightforward victory having taken the opening set against Slovakia's Magdalena Rybarikova.
Rybarikova stormed back to take the second set to love and grabbed an early break of serve to seize the initiative in the decider.
And it was the Slovakian, ranked 34 places above Watson, who held firm to close out the match despite a couple of scares and make it a third defeat for the British women.
Broady was up against Su-Wei Hsieh, the world number 72, who proved too strong for the British number three, Hsieh coming through 6-1 6-2.
However, there was also a terrific victory for British number four Moore, who came through qualifying to reach the first round proper and recorded a straight sets win against world No111 Donna Vekic.
Moore is ranked 280th in the world but joins Konta in the second round. Her 6-2 7-5 victory over Croatia's Vekic sets up a last-16 meeting with eighth seed Christina McHale.
Fourth seed Monica Puig and third seed Caroline Wozniacki came through their opening assignments with straight sets victories on Monday.