Card sharp Sheringham, who has turned his competitive instincts to playing poker since hanging up his football boots, knows Beckham's game better than most.
And ahead of the Champions League last-16 first-leg clash at San Siro on Tuesday, Sheringham reckons there is nothing veteran midfielder Beckham likes better than overcoming the odds.
Sheringham was a striker who thrived on crosses and Beckham's pinpoint accuracy was a dream supply line for him in the late 90s.
It was Sheringham who flicked Beckham's corner down for Ole Gunnar Solskjaer to score the iconic winner in the 1999 Champions League final against Bayern Munich.
And having also been in the United squad with Beckham after the midfielder's nightmare 1998 World Cup experience - when he was sent off against Argentina - Sheringham knows the 34-year-old thrives in adversity.
He said: "First of all Beckham will want to make an impression on the game.
"He'll want to let Sir Alex and the United fans know what they've been missing for however long it is he's been away.
"He'll want to prove to Sir Alex that it was a mistake to sell him. And David Beckham is good at proving people wrong. He's good at bouncing back and showing how good he is."
Sheringham, though, is quick to point out that United boss Sir Alex Ferguson should be well placed to deal with the Rossoneri wide man.
"Sir Alex knows all about David Beckham. He knows his good points and his bad points. And if Beckham plays on the right side of midfield, Ferguson will be telling Patrice Evra to get as tight as possible, because he won't be able to run him.
"He'll be saying don't let him get the ball on his right foot, because if he does he's dangerous."
United's form has been inconsistent this season but they are still well placed in the Champions League, Premier League and Carling Cup.
The one blot on the campaign so far was the painful third-round FA Cup exit to old rivals Leeds. That defeat, according to Sheringham, has cost United that chance to recreate a true treble.
"Without being funny, even if they win everything they are left in, it's not like the proper treble is it?
"It would be lovely for them to win the three trophies and they are in good positions in the Premier League and the Champions League, so why not?
"I don't think they are as consistent as they have been in previous years but then nobody is. Perhaps it's because so much money has been spent around the league that people are getting closer.
"People like Tottenham, Aston Villa and Man City have spent a lot of money and that improves their challenge.
"I want United to win. I think it will be close between United and Chelsea for the Premier League and I really wouldn't rule Arsenal out at the moment.
"They're very good at beating the smaller teams and they pass the ball very well."
Sheringham scored the equaliser against Bayern in 1999 before setting up fellow forward Solskjaer for the winner.
Those two, along with Andy Cole and Dwight Yorke, provided a formidable strike quartet. So how does Sheringham rate United's current front-line duo Wayne Rooney and Dimitar Berbatov?
"I've always thought Rooney is a fantastic player. Even more so now, and that's just down to the fact that he's maturing. It takes you a few years to understand what you can and what you can't do on a football field.
"He's coming of age and he's in his prime at an early age. The next three or four years hopefully he'll be even better."
While Rooney is having the season of his life with 21 Premier League goals already, Berbatov is still struggling to win over the Reds faithful.
But Sheringham, famed for his canny play and football brain, is a big fan of the Bulgarian's style.
He added: "I love the way Berbatov plays. I love what he sees and the way he glides at his own pace on the pitch.
"That's not to say that he's not working hard - because I was labelled a bit in the same manner. But when you've got the likes of Rooney, and Tevez last year, racing around it may be looks a certain way.
"I think people should realise what he does give to the team rather than what he doesn't. He's like poetry in motion when things are going well."
Sheringham retired from football in 2008, but enjoys playing cards and is now sponsored by PokerStars.
He admits he was schooled in the arts on coach trips during his playing days and said: "The only ones that played poker at United were Dwight Yorke and Mark Bosnich - I took them to the cleaners on many occasions. The likes of Beckham were too busy clinging on to their money!"
He might not be one for cards but there can be no doubting Beckham's enduring passion for football.
Ferguson and United will be hoping he has no surprises up his sleeve at San Siro.
Teddy Sheringham was taking part in PokerStars UKIPT Manchester
What do you think? Have your say.
Source: Manchester Evening News