Media playback is not supported on this device
The ultimate childhood tennis dream had been realised in one perfect draw - a Wimbledon wildcard leading to the British teenager facing the legendary Martina Navratilova on Centre Court.
It was 1994 and set to be nine-time champion Navratilova's farewell appearance in singles at the All England Club.
World number 360 Taylor, then 19, was steadily climbing the rankings, had just beaten a player in the top 50 at Eastbourne and would normally have had the unwavering support of the home crowd.
But ruining a legend's day would not have gone down well.
"When we came out they gave her a standing ovation for what seemed like forever, so I stood at the net like a doughnut waiting for her," Taylor, now Claire Shepherd after marrying Dean in 2013, told BBC Sport.
"It didn't stop; it was incredible. I was just stood there and the umpire said: 'It's OK, this doesn't normally happen.'
"The crowd were definitely pro-Martina, but they were still supportive of me.
"It is just a bit of a regret that my career highlight was losing a match. I don't like that really, but it was Martina on Centre Court."
Now a tennis coach, Shepherd, 42, is still very much in love with the sport and remains a regular visitor to SW19, having been hooked long before she became Oxfordshire county champion at the age of 10.
She used go to the All England Club with her tennis-mad father Phil and join the queuing masses to get tickets, so being out on the showpiece court in front of millions watching on television felt "very strange".
The Banbury-born left-hander had made her Wimbledon debut in the ladies' doubles in 1993. But this was something else.
"We had queued many times to watch Martina so to play her was amazing," the former British number two added. "My first thought was: 'Wow, that's great.' Then, it was: 'No hold on, that's a terrible draw.'"
The innocence of youth certainly helped to deal with facing one of the greatest players ever to pick up a racquet. Navratilova won a total of 18 singles Grand Slam titles during her astonishing career.
She may have been 37, but she was the world number four and still a dominant force on the All England grass, which was effectively her home turf.
"I was a little bit blasé," Shepherd explained. "At 19, you have a certain amount of naivety and just want to get on and do it. You just play the ball; it doesn't matter who is at the other end.
"I didn't think: 'I'm going to win, it's all fine.' It is difficult to have that bravado when you respect someone that much. But I didn't think: 'I'm going to get absolutely hammered.'
"I was well aware of how incredibly good Martina was. I would have to have had a lot of things fall in my favour but there was always that chance.
"I knew I was playing well; I had won a lot of matches and beaten Shaun Stafford, who was top 50 in the world, in the build-up. There was no point worrying about what she was doing."
Shepherd struggled to settle early on and trailed 5-1 in the first set. But she won four of the next seven games.
"I was leading 3-2 in the second because I broke her," said mother-of-two Shepherd. "But she stepped it up a gear and that was the end of it really."
Navratilova won that first-round match 6-2 6-3 and went on to the final before losing to Spain's Conchita Martinez. It was not quite the legend's final singles appearance at Wimbledon, as a wildcard gave her the chance to return in 2004, when she reached round two.
Media playback is not supported on this device
For Shepherd, it was back to the "undertour" as she tried to build on her successful career at junior level, which really got going at a national level around the age of 16.
It was around then that Taylor started to reap the rewards of an attacking philosophy, an approach that brought her the title of junior national champion at the age of 18.
"My dad always encouraged me to play aggressive tennis and go for my shots," said Shepherd, who now coach aspiring juniors at Virgin Active in Chiswick, west London. "He said that it would take a bit of time for more balls to land in than went out and that started to happen."
She continued to progress, pushing towards the top 150 in the world, playing singles at Wimbledon two more times, becoming British number two, and winning several lower-tier titles.
A senior national title eluded her, although she was a runner-up, before an ongoing elbow injury meant she had to retire in 2000 at the age of 25.
"I had tried to come back, but the injury never healed," Shepherd said. "It was really difficult. I just loved playing and was always so positive. I felt lost but I threw myself into coaching."
She had to give up her second career for a time to bring up her two young children after getting divorced. Harry is now 16 and Mathew 13 and, although both are sporty, they are not tennis-obsessed. It's the best juniors at her west London workplace who benefit from her expertise.
The next generation have widespread access to facilities and affordable coaching that often eluded youngsters during the 1980s and 90s. The budding Shepherd had to wait until dusk to get court time because juniors were way down the priority list.
That has changed in recent years and British tennis, with Andy Murray and Johanna Konta leading the way, is enjoying a boom period.
Media playback is not supported on this device
"I'm very fortunate doing what I do," Shepherd said. "Most of the juniors I teach have aspirations to achieve something in tennis."
And her own memories and love of all things Wimbledon remain as strong as ever.
"In 2012, I worked for the LTA for a while and went on before matches to do on-court demonstrations," she said. "All the emotion came back.
"People have dreams but not everyone gets to live them out. I lived it out and when I walked out I was sobbing. The children were looking at me and thinking: 'Why is that woman crying?'"
But the standout moment of 1994 is a non-tennis one.
"What made the day was that after the match and the interviews Martina talked to my mum [Janet] and dad, who were allowed to sit in on her press conference," Shepherd recalled.
"For someone of her stature to do that was the most impressive thing. It meant so much to my mum and dad.
"She didn't have to to do it. I wasn't even there so it wasn't for show; she is just a genuinely nice person, as well as an incredible tennis player."
Feeling like a "doughnut" while she waited for the biggest day of her career to get going wasn't really in Claire Taylor's planning.