Heather Watson was among three Britons beaten in the first round of qualifying for next week's Australian Open.
The British number five lost 7-6 (7-4) 6-3 to Spanish world number 145 Aliona Bolsova as she failed to reach the main draw for the first time since 2011.
Watson, 30, who reached the Wimbledon fourth round last year, has now failed to qualify for a second Grand Slam in a row after missing out at the US Open.
Compatriots Sonay Kartal and Paul Jubb also lost in Melbourne on Monday.
Kartal, 21, was beaten 4-6 6-3 1-6 by American Elizabeth Mandlik, while 23-year-old Paul Jubb lost 3-6 6-1 4-6 to Dalibor Svrcina of the Czech Republic.
Qualifying continues on Tuesday (23:00 GMT Monday), with Britons Lily Miyazaki, Katie Swan, Jodie Burrage and Katie Boulter in action.
They will hope to join Harriet Dart and Emma Raducanu as Britain's representatives in the women's singles main draw, although 2021 US Open champion Raducanu is still recovering from an ankle injury.
In men's qualifying, Britons Liam Broady and Ryan Peniston face Ecuador's Emilio Gomez and Canada's Alexis Galarneau respectively on Tuesday.
The pair could join Cameron Norrie, Dan Evans, Kyle Edmund, Andy Murray and Jack Draper in the main draw of the men's singles at the opening Grand Slam of the year.
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