After leaving Tottenham Hotspur in search of club honours with Manchester United, he managed to choose the first time in three years that no trophy found its way to Old Trafford by the season's end. Sheringham's own form dipped, so much so that the man bought to replace Eric Cantona was no longer certain of his place in Alex Ferguson's team. Inevitably questions were soon being asked about Sheringham's automatic right to partner Alan Shearer in England's attack, especially given the form Michael Owen was showing for Liverpool.
Then, on the eve of the World Cup, Sheringham's unscheduled golfing trip to Portugal, which involved a late night appearance in a local club captured for posterity and the tabloids by an alert photographer, put his place in Glenn Hoddle's squad for France in jeopardy. In the end a humble apology to all and sundry was deemed sufficient and Sheringham duly took his place for England's first game against Tunisia.
But after hitting the bar in the first half, he faded and was replaced by Owen although he kept his place ahead of the Liverpool man for the next match, against Romania, a decision which still rankles with Hoddle's critics. During the defeat in Toulouse he and Shearer looked totally out of sorts and once again Sheringham gave way to Owen, who promptly scored and kept his place in the side to stunning effect.
Sheringham admitted yesterday it had been hard to get over the last six months, a situation that has hardly been eased by starting only two games, both away in Europe, for United this season. "I was disappointed with the end of last season and the World Cup," he said.
"But players have these lulls in their performances and it's all about bouncing back from that. It took a long time to get over the World Cup to be honest, both mentally and physically, after a long season as well where we came away with nothing."
As a consequence of his inactivity Sheringham has found himself doing a lot of watching from the sidelines, something he is not accustomed to. But he said: "I don't mind watching because you can learn quite a few things. It's not always the same when you're playing a game as when you're watching and you see your team-mates doing different things. But I'd rather be playing."
Competition for places in United's attack has been made even keener by the arrival of Dwight Yorke. Asked whether he felt he and Yorke could form an effective partnership, Sheringham replied: "That's up to the manager to find out, but all three of the others are good strikers and I think I could gel with any of them."
His chances of adding to his 36 England caps on Saturday against Bulgaria seem limited to the role of the substitute he played in England's last game in Stockholm, where he came on for the last 15 minutes, although if he recovers from his own knee injury it is not inconceivable that the injury to Paul Scholes, his United team-mate, could pave the way for Sheringham to return, albeit in a slightly different role.
"He is an astute player who probably suits international football more than anyone we have in the squad," Hoddle said yesterday. But whatever the England coach has in mind Euro 2000 is likely to be Sheringham's last tilt at an international tournament.
"Maybe," he admitted. "But I think everyone's got to look at it that way, especially when you're playing for England because you never know what's around the corner - especially when you get to my age." At 32 life for a footballer often does take on a different perspective, and in Sheringham's case that will manifest itself in next week's launch of his autobiography, the latest in a series that might be entitled The England Books, which began with Hoddle's own World Cup diary. The fuss that surrounded that, and Tony Adams' autobiography, overshadowed the build-up to the Sweden match, but Sheringham feels it is no longer an issue.
"I think it's all calmed down a bit," he said. "It's all about getting results now, that's the main thing. We've talked about the Sweden game and there are things we can learn from it. It was a terrible result for us but you can take good and bad from it.
"Bulgaria will make it difficult for us on Saturday and we'll have to be very patient. I know they got a terrible result in their first game, but they'll still be hard to break down. Most Continental teams just sit back and look as though they're not bothered, then all of a sudden there's a quick break and you're caught napping.
"I'm sure they'd be happy with a draw but we've got to be very watchful." And for Sheringham, the watching brief seems likely to last a while longer.Reuse content