The year 38-year-old Kimiko Date Krumm last played at Wimbledon the Spice Girls had their first UK number one single and Bill Clinton was re-elected president of the United States.
Despite her age, the Japanese player gave 18-year-old Danish opponent Caroline Wozniacki a run for her money on her return to the tournament, taking the first set and going 3-1 up in the second before tiredness and injury got the better of her.
As Date Krumm grew more weary, world number nine Wozniacki, who was born a year after Date Krumm made her first Wimbledon appearance, came into her stride, taking the opportunity to get back into the contest and win 5-7, 6-3, 6-1.
The pair were evenly matched for most of the first two sets, taking it in turns to break serve and keeping the crowd on the edge of their seats with long rallies and well placed shots.
But an hour and a half into the match Date Krumm, cheered on by racing driver husband Michael Krumm, was beginning to look increasingly weary and in pain, stopping to stretch her leg against the umpire's chair while her trainer was called out.
Spectators fanned themselves with sunhats as the match was interrupted for a medical break while a physio treated Date Krumm's legs with an ice pack.
But the former world number four, who came out of retirement last year and has not played at Wimbledon since 1996, failed to regain her momentum.
Grimacing with every shot Date Krumm slowly crumpled and Wozniacki, fresh from winning her fifth career singles title at Eastbourne last week, ran away with the match, breaking twice to win four straight games and the final set.
