Everyone remembers their first football match. Mine was a 1-1 draw between Tottenham and Leeds in May 1995. I was only six years old so I don’t recall the finer details, but I do remember this being a big deal because it was Jürgen Klinsmann’s last game for Spurs (although he would later return on-loan to save the club from relegation and force mouthy chairman Sir Alan Sugar to eat a large slice of humble pie). Klinsmann failed to mark the occasion with a goal, but some bloke called “Teddy” did net one. This was my first introduction to Edward Sheringham.
Sheringham was a star from the outset. In the inaugural Premier League season he claimed top scorer with 21 goals for Tottenham Hotspur and one for former club Nottingham Forest. But it was not just his finishing that made Teddy such a valuable asset. A wily and underrated forward, he was adept at holding up play, finding space and playing the killer pass.
Sheringham’s fine form earned him a starting place in the national team, back when England were a likeable and half-decent side – which is considerably more than can be said for today’s squad. As England’s number ten, he formed a strong partnership with Alan Shearer during Euro 96. The pair displayed their prowess most memorably by notching up two goals each in the famous 4-1 demolition of Holland.
Teddy had become a true Spurs legend over the years, but the fans’ adulation could not dispel his quiet but firm ambition. With Tottenham incapable of delivering the trophies he so desperately craved, Sheringham transferred to Manchester United in June 1997 for a fee of £3.5 million.
Drafted in to replace the suave Kung Fu master that was Eric Cantona, Sheringham endured a patchy first season in Manchester. A missed penalty on his debut against Spurs delighted many former fans, but Teddy did not take long to rediscover his form. By 1999 he had established himself as an integral member of United’s historic treble-winning team. At last Sheringham satisfied his hunger for silverware; proudly collecting Premier League and FA Cup winners’ medals – the latter secured by his opening goal in the final at Wembley.
But it was the Camp Nou that would witness Teddy’s finest hour. On literally the biggest of stages, Sheringham played a crucial role in United’s legendary comeback against Bayern Munich in the Champions League final. Having come on as a second-half substitute, he scored a dramatic last-minute equaliser and then provided the assist for Ole Gunnar Solskjaer’s injury-time winner. This was the moment when Sheringham transformed himself into a true cult hero.
Like the evergreen Ryan Giggs and Paul “never-learned-to-tackle” Scholes, Sheringham played some of his best football in his later years at Old Trafford. In the 2000-01 season, at the age of 35, he was named Player of the Year by both the Football Writers’ Association and the Professional Footballers’ Association.
Although he set the template for United poaching Tottenham’s most promising players (see Michael Carrick, Dimitar Berbatov, and hopefully not Gareth Bale), Teddy redeemed himself with the Spurs faithful by returning to White Hart Lane in 2001.
Never the fastest player, Sheringham overcame his lack of pace with a brilliant reading of the game. This enabled him to continue playing until the ripe age of 42, without having to drastically alter his style of play.
Upon leaving Spurs once again, the veteran striker capped an impressive career with further spells at Portsmouth, West Ham (having begun his career at Millwall, Sheringham was one of few footballers foolhardy enough to play for both the Hammers and their bitter East End rivals) and finally at Colchester United.
While few, if any, footballers make the perfect role model, Sheringham’s tireless commitment and obvious love for the game endeared him to fans for over twenty years throughout his career. The antithesis of the archetypal snood-wearing, airgun-wielding modern footballer, Teddy was intelligent, modest and kept a relatively low profile off the pitch. Mario Balotelli he was not.
A penchant for sports cars and glamour models betrayed his laddish side, but he still retained a bit of class – more Michael Caine than Danny Dyer. He was driven more by ambition than money, and always handled his private life with a tad more dignity than the likes of John Terry or Wayne Rooney.
Since finally succumbing to retirement, Sheringham has indulged in his love of poker, a game which requires the same mental sharpness and competitive nature that made him such an effective footballer. He’s not bad either: last year Teddy finished fifth in a major tournament in Portugal, claiming winnings of €93,121 in the process.
Apparently he pledged the money to charity, but reneged when a local car dealer tempted him with a brand new Aston Martin DB9. Maybe scratch that “antithesis to the modern footballer” bit then. But he was still a bloody good striker.