He was constantly jeered - "Judas" was the politest chant - and was having a truly awful game. Then came the chance of redemption as Justin Edinburgh gave away a foolish penalty.
Sheringham, with a good but hardly flawless penalty record, stepped up to take it. Behind the goal Spurs fans waved their arms in an attempt to distract, on the goalline Ian Walker jumped about with similar intent. Sheringham thudded the kick against the base of a post, then thrashed the rebound over. Even if he had scored with the second shot it would not had counted as Walker had not touched the ball. Spurs exulted, Sheringham looked devastated.
Twenty minutes later he was seized with joy as his hopeful shot took a fortunate deflection and landed at Nicky Butt's feet yards from goal. So enraptured was Sheringham at the subsequent goal that Graham Poll, the referee, had to drag him away as he taunted Allan Nielsen. He settled for raising his arms, very obviously, to the heavens.
A minute later Sheringham's pleasure was complete as David Beckham's cross floated over Ryan Giggs only for Ramon Vega, who had given Sheringham a fearful whack earlier on, to inadvertently divert the ball past Walker with his thigh. United thus went top of the embryonic Premiership table while Tottenham fell to its bottom.
"Those goals were a bit of a relief," admitted Sheringham. "I felt confident taking the penalty and I'll take another." Alex Ferguson, United's manager, confirmed that if his team get a penalty against Southampton on Wednesday Sheringham would be given the responsibility.
United's goals may have been fortuitous but they were deserved. An even, largely disappointing first half had given way to a United siege in the second. Were it not for the magnificent Sol Campbell Tottenham would have been beaten long before Butt scored.
They had three debutants but only one, 19-year-old Stephen Clemence, son of Ray, impressed. He showed enough neat and thoughtful touches in midfield to suggest Darren Anderton's continued absence may not be as debilitating as feared. However, he tired in the heat and any inspiration Spurs had went with him.
The other new faces, the pounds 8m pair Les Ferdinand and David Ginola, were almost anonymous. Ginola saw plenty of the ball but did little of note with it. Ferdinand was consistently outjumped by Gary Pallister as Spurs succumbed to the obvious temptation of lumping high balls towards him. It did not help that they usually did so from deep rather than making the byeline.
United were also tempted into playing the long ball early on as the packed midfield and extreme heat cramped space and movement. However, without Andy Cole they were no more likely to succeed that way than Spurs.
Cole was absent after undergoing an operation for a boil on his backside. The operation, done on Friday, is likely to keep him out for 10 days. Given the amount of time he has spent on the bench over the last few years it was a surprise Brian McClair did not need one as well.
Although Peter Schmeichel did have to catch a tame effort from Ferdinand as he attempted to reach one through ball after 11 minutes it was 10 further minutes before either goalkeeper was seriously troubled. Then Schmeichel got down well as Vega fired through a crowd of players from 25 yards.
Vega had also headed over before United finally tested Walker after 29 minutes. A Schmeichel clearance was flicked on by Jordi Cruyff and Sheringham, with his first decent touch, forced his former team-mate into a diving save at the near post.
Spurs had one more effort, a penalty shout after Paul Scholes had bundled Vega over early in the second period, before United took control. Sheringham wildly mis-kicked when set up by Scholes then Campbell denied Roy Keane and Cruyff in succession.
Then came the missed penalty, after which it seemed no-one would score. "I thought we had missed our opportunity," said Ferguson, who reacted by sending on Beckham. Indirectly this did the trick, Beckham providing the pass for Sheringham's ultimately deflected shot and for Vega's own goal. "Two-nil without Cantona," sang the United fans.
"They are going to be the team to beat," said Gerry Francis. "They remind me of the Liverpool team that dominated in the 70s and 80s."
Goals: 0-1 Butt (81), Vega (og 82) 0-2.
Tottenham Hotspur (4-4-2): Walker; Carr, Vega, Campbell, Edinburgh; Nielsen, Howells, Clemence (Sinton, 73), Ginola; Ferdinand, Iversen. Substitutes not used: Calderwood, Scales, Fenn, Bardsen (gk).
Manchester United (4-4-2): Schmeichel; Irwin, Johnsen, Pallister, P Neville; Scholes (Beckham, 65), Butt, Keane, Giggs; Sheringham, Cruyff. Substitutes not used: Poborsky, McClair, G Neville, Van der Gouw (gk).
Referee: G Poll (Tring).
Bookings: Tottenham: Vega. Manchester United: Scholes.
Man of the match: Campbell.