Alex Bogdanovic, Jamie Baker and David Rice all lost in the second round of Wimbledon qualifying in a disappointing day for British players in Roehampton.
British number five Bogdanovic, who has played eight times at Wimbledon, lost 7-5 2-6 6-3 to Evgeny Korolev.
Baker was beaten 6-7 (5-7) 6-3 6-4 by Igor Kunitsyn while Rice fell 6-3 6-4 to Flavio Cipolla.
Britain will only have three male players in the main draw: Andy Murray, James Ward and Kyle Edmund.
In the women's qualifying, there were first-round defeats for Lisa Wybourn, Emily Webley-Smith, Amanda Carreras, Anna Smith and Melanie South but Naomi Broady and Jade Windley won.
Broady beat Stephanie Dubois of Canada 6-2 7-6 (7-4), while Windley eased through 6-4 6-4 against Croatia's Tereza Mrdeza.
Wybourn lost 6-1 7-6 (7-5) to 10th seed Vania King of the US and Webley-Smith was defeated 6-3 6-3 by Slovenia's Tadeja Majeric.
Carrera lost 6-2 7-5 to 15th seed Teliana Pereira of Brazil while South was thrashed 6-2 6-0 by Israel's Shahar Peer.
There were also defeats for Anna Smith, beaten 6-2 6-4 by Slovakian Anna Schmiedlova, and Katy Dunne, who went down 6-3 6-2 to Italy's Nastassja Burnett.