World number one Naomi Osaka followed up her early French Open exit with a shock second-round loss to Kazakhstan's Yulia Putintseva in Birmingham.
The Japanese 21-year-old lost 6-2 6-3 to her world number 43 opponent.
US Open and Australian Open champion Osaka was beaten by Katerina Siniakova in the French Open third round.
Earlier in the day, Roland Garros champion Ashleigh Barty, 23, reached the Birmingham quarter-finals after defeating American Jennifer Brady.
The Australian, who claimed her maiden Grand Slam singles title in Paris, won 6-3 6-1 against the world number 66.
The Birmingham Nature Valley Classic is one of several grass-court tournaments taking place before Wimbledon begins on 1 July.