Predictably, when asked by Sky Sports who would make the best team of players he faced, the ex-Manchester United and Tottenham striker packed his formation with some of the finest talents of the last two decades.
But there are some names that might surprise you, including a defender who Sheringham insists was a nightmare for any centre-forward.
England's former No. 1 faced Sheringham in countless tense clashes for Arsenal, and the pair also played together for the Three Lions. "He was just a great 'keeper who made things look so easy. You could hit shots in the top corner and you would think that's a goal and he would just go across," he explained to the Fantasy Football Club.
Another man who played with and against Sheringham in the Premier League, and a stalwart of Manchester United's unbeatable team for over a decade. "I picked him in my team as well, and what a class act on and off the pitch. Top, top player, right back, left back, could get forward and defend and I never saw him have a bad game, always 8.5 out of 10 every week, every game that I played in."
A World Cup winner with Italy, Cannavaro was one of the most formidable centre-backs of his generation. "I played against him a few times for Italy. Not the biggest, quickest, strongest, but what a football brain. So clever with his positional sense, organising the defence, and that is exactly what I like as a centre-half."
The former Sheffield Wednesday, Nottingham Forest and England defender is a strange name to see amongst a team of world-renowned names. But Sheringham insists there were few defenders his equal: "This guy, week in, week out, was a 9 out of 10 and I do not ever recall seeing him having a bad game. Just a class act and no one could ever beat him."
A man that needs no introduction, the full-back helped torpedo England's dreams of World Cup success in 2002 with a quarter-final win on the way to glory. "Epitomised the way Brazil played at the time he was in the team. They had two centre-halves and two solid midfield players and they used to let the full backs bomb on, always shooting and crossing," Sheringham said.
Volatile, tenacious and utterly committed, the Ireland international was the beating heart of Sir Alex Ferguson's all-conquering United team. Sheringham admitted: "If he was not playing in the Manchester United team with all those fantastic players we had, the team would not have been the same."
A veteran of those legendary Manchester United-Arsenal clashes that tended to decide the Premier League champion at the turn of the millennium, Sheringham has nothing but respect for his old adversary. "You need players like this in your team in the Premier League and this is why Arsenal are struggling at the moment, and maybe even Man Utd a little bit."
Few eyebrows will be raised at the sight of the incomparable Zizou in this team. "6ft 3in, but so graceful and moved so poetically with the ball at his feet," Sheringham said.
"We played against him for Man Utd against Juventus in my first Champions League game and we beat them that night, but he was phenomenal."
The Dutchman is usually credited, along with Arsene Wenger, for turning Arsenal from a Premier League also-ran to one of it's most formidable outfits. "Class act, harder than people give him credit for as well, a nasty player and scored fantastic goals," Sheringham recalled.
The little ex-Napoli and Chelsea man usually figures in the pantheon of great imports that made the Premier League one of the world's most enthralling football competitions, alongside the likes of Bergkamp and Eric Cantona. "He played the role off a centre-forward. The way he manipulated the ball, he scored free kicks, a legend at the Bridge and you have to take your hat off to these players."
At his best, one of the finest forwards ever to set foot on a football pitch. "There was only one man for me to pick up top, The Ronaldo," Sheringham said.
"If you are talking about players on a different planet…. He came to Old Trafford one time for Real Madrid and scored a hat-trick, just different class, he came alive when the ball was around the penalty area.