As the fortunes of the young Scotsman waned, he had a long way to fall. Apart from being contemporary amateur champions, what Sherry and Woods have in common is that they stand out in a crowd. "Just look at me," Sherry said. "I'm 6ft 8in, I've got ginger hair and my name's Sherry."
Indeed, in 1995 most people thought a great British Sherry had been untapped. While studying at Stirling University he began to play some seriously good golf. At the age of 21 he won the Amateur Championship and was fourth in the Scottish Open, the finest performance by an amateur in a European Tour event. Had he been a professional he would have won pounds 30,000. As it was he took pounds 1 off Tiger in a bet. In the Open Championship at St Andrews he had again finished ahead of Woods, and he capped it by leading GB and Ireland to a resounding victory over the United States in the Walker Cup.
"It was a great year," Sherry said, "but I was only an amateur. It's all in the past. People still come up to me and say you're the man who beat Tiger Woods, but I wasn't out to do that. We've had a laugh about it. We didn't think we were different from anybody else. We thought we were normal guys hitting a golf ball. What Tiger's done since is fantastic."
What happened to Sherry was the opposite. After turning professional in 1996 he was laid low by glandular fever. "I was run down. I was finishing my studies and at the same time flying here, there and everywhere. My first year as a professional was wiped out. People described it as a disaster which is absolute nonsense. What happened at Dunblane was a disaster."
The fact that he is Scottish has not made life easier. If Sherry had been born in, say, Redditch he would have been left alone once the initial fuss had died down. The Scots have their own agenda and nobody had a bigger profile than Big Gordie. It was news if he made the halfway cut and bigger news if he didn't.
"I'm learning all the time. A lot of people are just looking for scandal. A couple of years ago I saw a billboard saying 'Sherry in fracture tragedy'. The story was about me breaking my leg but that happened when I was 13."
There is, however, a plus side to the high profile. Despite the fact that he has failed to get his tour card at the Qualifying School, Sherry has four sponsors. "And my mum and dad," he added. "They're my biggest supporters." His mother Anne works with handicapped children at a school in Kilmarnock, his father Bill is a retired policeman. "When I got low I took it out on my parents," Sherry, who lives at home, said. "A lot of things happened that shouldn't have happened and my mum and dad had to deal with it. It's made us closer."
After a re-evaluation this year Sherry (he got a degree in biochemistry) is attempting to secure his card via the smaller, less glamorous Challenge tour where a lot of the glare can be shut out. This week he will play in the Ivory Coast Open which has a prize fund of pounds 70,000 compared to the pounds 770,000 purse for the Dubai Desert Classic.
"One of the mistakes I have made is to accept invitations to play on a regular tour, splitting my time with the Challenge tour. You get caught in no man's land and you lose your edge. That's why I've decided to play the Challenge tour full-time.
"It's a bit of a culture shock. There's nothing laid on. The cost can be astronomical, even more than on the regular tour. But it toughens you up. As Jack Nicklaus said, you've got to learn how to lose before you can win. I've been through rough times and I think I know how to cope with it. It makes you mentally tougher. To me playing on the Challenge tour is not a negative thing. I'm totally positive."
Sherry, who has been working with Greg Schofield at Gleneagles, was in sparkling form over Christmas, a return to full fitness coinciding with victory in the Mauritius Open. With a first prize of pounds 3,000 it may be regarded as small beer but not by Sherry. It was his maiden victory as a professional.
"The second round was played in a hurricane and I shot 66 so I was absolutely delighted. It's been a long time coming. Over the last few holes my concentration went because I was thinking of what I was going to say for my victory speech."
And an old school pal, Angus Mitchell, was caddying for him. "It was his first time on a golf course and he was more nervous than I was. We almost got to the point of choking. When I rang mum and dad they were ecstatic and it was my mum's voice that made it so special."
The success was toasted in champagne but Sherry and alcohol don't mix. "They said 'Go on big man take a swallow' but I couldn't. I nearly threw up. What was fantastic was learning to win again. Sometimes you want to win so badly it can affect you. You have to learn to channel your distress in the right way. If I don't play well I'm still hard on myself because I know what I'm capable of."
On Thursday the Ivoire Golf club in Abidjan will have the pleasure of the company of the Mauritius Open champion. The following week he's off to Nairobi for the Kenya Open. "I don't intend," Sherry says, "to do this every year."