Five-time Wimbledon champion Venus Williams was knocked out in the first round of the Bad Homburg WTA grass court event on Monday but Japan's Naomi Osaka breezed through.
Williams, 46, is due to play doubles with her sister Serena at Wimbledon, which starts in a week's time, and was also given a wildcard to enter the Bad Homburg singles.
She took her time to get going against qualifier Irina-Camelia Begu of Romania, losing the opening set 6-2 before battling back to take the second 6-4.
Williams led 5-3 in the decider and was two points from victory at one point but Begu dug in to force a tie-break, which she won 8-6.
Sixth seed Osaka, 28, had little trouble seeing off Pole Magdalena Frech 6-4, 6-1.
Sealed in style ✨@naomiosaka is into the Round of 16 in Bad Homburg after defeating Frech 6-4, 6-1!#BadHomburgOpen pic.twitter.com/yeBh4eaSK7
— wta (@WTA) June 22, 2026
The first set was close until a rain-enforced break at 5-4, after which, the four-time Grand Slam champion lost only one more game.
Osaka has never won a grass court tournament, with her best result a semifinal at Nottingham in 2018.