Teddy Sheringham was a prominent figure in the world of football during the 90s and 00s, with his on-pitch success capturing the attention of the media. However, it was his off-pitch escapades that truly garnered front-page headlines.
Having kickstarted his career at Millwall in 1983, the now 59-year-old sports icon enjoyed stints at Nottingham Forest, Tottenham Hotspur, and Manchester United, in addition to representing England from 1993 to 2002.
Despite his accomplishments on the field, Teddy also gained notoriety for his reputation as one of the most notorious partygoers in the Premier League, with a string of scandals involving various controversies, including romantic entanglements, legal issues, and disputes over child support.
His high-profile romances with glamour models Katie Price and Danielle Lloyd were well-documented while he was also subject to kiss and tells lauding his manhood and bedroom prowess – all against the backdrop of legal battles with his ex.
Add the scorn of bosses over his wild nights out, Teddy was usually to be found in the eye of a perfect storm.
A slew of high-profile romances led him to scandal, including his relationship with Danielle Lloyd (the couple pictured in 2006)
Teddy Sheringham’s illustrious career made him a hit on the newspapers’ back pages in the 90s and 00s – yet it was his wild antics off-pitch that landed him on the front (Teddy pictured after the FA Cup final in 1999)
Teddy was often pictured with an array of women and became known for his lothario ways (pictured outside Funky Buddha in 2004)
Drinking, clubbing and the infamous ‘Dentist’s Chair’
Ahead of the 1996 Euros, Teddy – alongside his troubled teammate Paul Gascoigne – was pictured on an extremely boozy night out in Hong Kong.
The group partook in ‘The Dentist’s Chair’ drinking game, in which the drinker reclines while alcohol is poured into their mouth from above.
The night was met with widespread fury from fans due to the proximity to the tournament and how their training could have been disrupted.
Teddy later spoke about the night, saying: ‘It was a great night out, yes. Great fun. I mean, you’re with 20 of your mates…
‘You know you have four weeks of staying in and are allowed this one night out. It’s not great pictures, I know, how it turned out. But you know you want to enjoy yourself for that one night — and we certainly did.’
He lauded England manager at the time Terry Venables for how he spun the incident – turning the blame to himself rather than the players.
Teddy revealed: We know it didn’t look very good to the public and Terry wasn’t best pleased about it and he let us know in no uncertain terms. But what he did afterwards with the Press was pure genius.
‘He said, ‘Look, I allowed them out; it’s on my shoulders.’ And he protected the players. He defended us and we loved him for it.’
Ahead of the 1996 Euros, Teddy – alongside his troubled teammate Paul Gascoigne – was pictured on an extremely boozy night out in Hong Kong (Teddy and Paul pictured in 1996)
He lauded England manager at the time Terry Venables for how he spun the incident – turning the blame to himself rather than the players (Ted and Terry pictured in 1994)
Nicky Butt, Teddy, David Beckham and David May (L-R) pictured in 1999
Following from the incident, in 1998 Teddy again took part in a late-night binge session in Portugal – a week before the World Cup Finals in France.
England boss Glenn Hoddle kept him in his squad despite axing colleague Paul Gascoigne for a similar incident.
His hard-partying again landed him in hot water in 1998 when revered football legend Sir Bobby Charlton slammed his raucous ways.
He said: ‘If the players don’t have the common sense to be able to behave themselves and act in a reasonably proper manner then it’s absolutely nonsensical to think we have a chance of winning the World Cup.’
Paying the (Katie) Price of fame
Teddy’s lothario ways came to hit the spotlight when he began an affair with then-up and coming glamour model Katie Price – known at the time by her moniker Jordan
Teddy’s lothario ways came to hit the spotlight when he began an affair with then-up and coming glamour model Katie Price – known at the time by her moniker Jordan.
The iconic star left her first boyfriend, an electrician, for a short-lived fling with the former Millwall striker in the late 1990s, before he was said to turn frosty.
She claimed at the time that the reason they went their separate ways was because ‘he went cold when the papers found out about us’.
The TV personality thought back to the moment she found out and told of how the agent informed her she had ‘made the front page’.
She said: ‘I went, ‘What do you mean? No! I haven’t told anyone,’ but she had stitched me up…
‘To this day I think Teddy Sheringham thinks that I sold that story and I swear on my life I never. I was so gutted because I did like him and I didn’t do anything.’
Child maintenance rows
Teddy was at loggerheads with his ex Denise Sims, when she accused the star of leaving her struggling to raise their then 11-year-old son Charlie on £125 a week – despite his whopping £22k a week pay check (Teddy pictured with Charlie in 1998)
Teddy was at loggerheads with his ex Denise Sims, when she accused the star of leaving her struggling to raise their then 11-year-old son Charlie on £125 a week – despite his whopping £22k a week pay check.
Back in 1999, after Teddy was awarded a £150k bonus for winning European Cup, Denise hit back about their family arrangements.
She said: ‘I heard Teddy say how he felt the Germans were flashy and giving him the hump…well that’s how I think about him…
‘Teddy is fabulously rich and I must admit he spares no expense when he takes Charlie out. He even took him along to Barcelona and to the celebrations in Manchester. But he is only a part-time father and for the majority of the time his son lives in near poverty.’
After revealing she was living in a small flat in Chingford, Essex and in mounting debt, she claimed Teddy had suggested he bring up Charlie alone and she pay him.
She went as far as threatening to take him to court, saying: ‘I only want what is best for my son. I want Teddy to pay for Charlie’s future.’I have been told the only way to force him to pay more is to go to court. I have no alternative.’
At the time, she revealed she was earning £100 a week as a part-time secretary and was receiving a £50 top-up on Family Credit.
Denise met Teddy when she was a barmaid in a South London pub. She was 20, he was 19 and after a romantic holiday to Gran Canaria Denise discovered she was pregnant at 23.
Revealing his shock reaction Denise said: ‘At first Teddy went ballistic. He couldn’t handle the fact I was pregnant. But I told him I was going to have the baby whatever happened and he finally came round’.
Charlie went on to become a professional footballer, playing for Crystal Palace, Waltham Abbey and Snodland Town among others.
She went as far as threatening to take him to court, saying: ‘I only want what is best for my son. I want Teddy to pay for Charlie’s future.’I have been told the only way to force him to pay more is to go to court. I have no alternative’ (Charlie and Teddy in 2002)
Fiancee who warned other women: ‘Don’t marry a footballer!’
Teddy split from his girlfriend of eight years Nicola Smith in 2001, due to ‘backstabbing’ and the loneliness of being a WAG.
At the time, she said: ‘I felt great relief when Teddy and I split – I had been so lonely it hurt. It had become so bad that just a week after I walked away from him I began to feel better.
‘People might think it glamorous, but believe me, a footballer’s life is very boring. When you add that to the backstabbing and the girls who try it on with him, you have to ask yourself if it’s really worth it.’
In 1998, during their relationship, Nicola was left bereft when he was caught in Portugal with a busty blonde.
Teddy split from his girlfriend of eight years Nicola Smith in 2001, due to ‘backstabbing’ and the loneliness of being a WAG (pictured in 1999)
Teddy and Nicola are pictured in 1994
She said: ‘There were times when we were out and girls were going out of their way to kiss Teddy in front of me. It does scare you because you think in the back of your mind “What if I am not here one day?”.’
‘People are only human at the end of the day. And when you have temptation thrown in front of you that often, how many times can you turn it down?’
Nicola’s jealousy was the root of many rows in their stormy love life. She says: ‘Sometimes our whole evening would be ruined because of this. It would cause arguments.’
Nicola, whose sister Mandy is the ex-wife of Rolling Stone Bill Wyman, issued a stark warning to WAG hopefuls, saying: ‘Dating a rich man is very different to going out with someone who is rich and a famous footballer…
‘When you walk in a room, every girl is trying to get his attention. And no amount of money can make that better.”
Police problems
In May 2007, Teddy was among a trio of West Ham footballers arrested for allegedly swapping speeding points to dodge a driving ban
In May 2007, Teddy was among a trio of West Ham footballers arrested for allegedly swapping speeding points to dodge a driving ban.
He was quizzed by police on suspicion of perverting the course of justice. His teammates Bobby Zamora and winger Shaun Newton were also arrested.
A Scotland Yard spokesman said at the time: ‘A 41-year-old man was arrested on May 15 on suspicion of perverting the course of justice when he attended, by appointment, an east London police station..
‘He was bailed to return on a date in July pending further inquiries. It is alleged he gave false details regarding an alleged speeding offence.’
In June, his lawyer Henri Brandman said: ‘For the avoidance of possible doubt, my client has not been charged with any offence…
‘He categorically denies the allegation that has been made. He has cooperated with the police. No further statement will be made by my client, his agent or I.’
It was later revealed that Shaun had offered to ‘lose’ speeding tickets at a price of £250, for which he was slapped with a suspended jail spell.
Glamour girl frolics
Once again Teddy’s steamy sex life hit headlines, when glamour model Emma Davies, then 20, regaled a night of passion with Teddy in forensic detail.
After meeting at a Birmingham nightclub, Lee Ryan’s ex Emma and Teddy frolicked in which she told The People was ‘the best sex of her life’.
In an explosive kiss and tell about the evening, she spoke about her admiration for the footballer’s physique and even told the paper he was ‘well endowed’.
She went as far as comparing Teddy to her Blue star ex-boyfriend, saying: ‘Lee was a great lover and very romantic, but with Teddy it was a totally different ball game. There was an intense power in his lovemaking and he really blew my mind.’
Emma proudly revealed their night of passion concluded with Teddy giving her £20 for a cab home and a kiss on the cheek.
Danielle and Teddy, then 23 and 40 respectively, had been dating for several months before the lothario left her – after which she admitted she was left devastated (pictured in 2006)
In 2006, Teddy and Miss Great Britain winner Danielle Lloyd were a hot new couple about town, but the relationship quickly ran into controversy when she was stripped of her title for posing for Playboy, and amid rumours she’d been dating the footballer who was on the judging panel of the contest.
He was the only judge to vote for Danielle, and she then secured the title via the public vote.
She insisted that they were not dating during the contest and had only met at the very end.
‘It was a total misunderstanding. Me and Ted met before the show I only spoke to him at the after party and we exchanged numbers,’ she claimed.
However, the relationship was set to be short lived regardless.
Teddy broke up with Danielle following her controversial appearance on Celebrity Big Brother in 2007 – during which she joined Jade Goody and Jo O’Meara in being accused of racist abuse toward their housemate Shilpa Shetty.
Danielle and Teddy, then 23 and 40 respectively, had been dating for several months before the lothario left her – after which she admitted she was left devastated.
Despite failing to deliver the news to Danielle in person, Teddy was spotted on the town after her eviction from the Big Brother house where he stated: ‘I am no longer with anyone. I am not with her tonight and who is to say I will ever be with her again?…
‘People keep asking if we are engaged yet but I can say I am not with anyone, I wish people would believe it. People don’t believe me but I guess they will have to read what she has to say in the papers from now on.’
On the same night he made his blunt statements, he was seen at Mayfair’s Funky Buddha nightclub flirting with revellers. An onlooker said: ‘He was trying to hide the girls at first but after a few Tiger beers he was flirting like an 18-year-old…
Teddy broke up with Danielle following her controversial appearance on Celebrity Big Brother in 2007 – during which she joined the late Jade Goody and Jo O’Meara in being accused of racist abuse toward their housemate Shilpa Shetty (Jo, Jade and Danielle pictured)
‘He was buying rounds of shots for the girls and seemed like he was having a great time. There was one brunette in particular who he was quite attracted to. As he ordered drinks he was nibbling her neck and didn’t look like he had anything at all to hide.’
Danielle later said leaving the CBB house was hard as she was faced with not only backlash for the racist abuse but also for the brutal dumping: ‘I got booed, it was horrible. It was heartbreaking. I just wanted everyone to like me, and they didn’t…
‘I was in a relationship and when I came out he basically disappeared and said he didn’t want anything to do with me. He was Teddy Sheringham…
‘That was obviously heartbreaking because it was the first normal relationship that I’d been in that wasn’t abusive, so it was really upsetting…
‘My world came crashing down around me. I thought I’d never work again, I was getting death threats, it was the worst time of my life.’
A new man
Hanging up his lothario boots, Teddy has now become the ultimate family man since marrying wife Kristina Andriotis in 2016 (the couple pictured in 2024)
Hanging up his lothario boots, Teddy has now become the ultimate family man since marrying wife Kristina Andriotis in 2016 after 10 years of dating.
Kristina is 20 years Terry’s junior. The couple share two children.
Their marital home is called Camp Nou, after the Barcelona stadium where he scored in Manchester United’s incredible Champions League final comeback of 1999 .
In a nod to their age gap, they reportedly once decorated the house with a sign that read: ‘An old rooster and a young chick live here.’
Kristina, who previously worked in PR, is just two years older than Sheringham’s footballer son Charlie.
As well as working as a football pundit for a number of international broadcasters of the Premier League, Teddy also acts as a club ambassador for his former clubs Manchester United and Tottenham.
Retirement has also seen Teddy reveal a secret talent of sorts.
In 2020, the Treble winner took part in reality series The Masked Singer as ‘Tree’.
