Andy Murray's first match of the grass-court season ended in defeat by American Marcos Giron at the Stuttgart Open.
Appearing in the 999th singles match of his career, three-time Grand Slam champion Murray was beaten 6-3 6-4 in the first round.
The 37-year-old is preparing for what looks set to be his final Wimbledon, having previously said he does not plan on "playing much beyond the summer".
Against Giron the former world number one twice saved break point in his first service game, before missing out on an early chance to break himself.
World number 54 Giron soon took advantage, breaking to go up 4-2 before comfortably taking the opening set.