Former world number one Venus Williams lost her 10th singles match in a row as she was beaten 6-2 6-4 by Kaitlin Quevedo at the Madrid Open.
Williams, 45, is the first former number one to lose 10 matches in a row since the rankings were first published in 1975.
The veteran last won a match last July when beating fellow American Peyton Stearns at the Washington Open.
Williams won Wimbledon five times between 2000 and 2008 and also won the US Open twice. She holds the record for most appearances at a Grand Slam, with this year’s Australian Open her 95th tournament.
Her younger sister Serena, 44, has not played since the 2022 US Open but has not officially retired.
The 23-time Grand Slam singles champion is eligible to play again after re-entering the out-of-comptetition drug testing pool but she has not announced an official return.
In contrast, 20-year-old Quevedo of Spain is ranked 140 in the world and was playing in her first WTS 1000 match.
The wildcard came from 3-0 down in the second set to defeat 2010 finalist Williams, who had won six of her eight Grand Slam titles before her opponent was born.