Teddy Sheringham: The Noughties’ Naughtiest Footballer – Heartbreak, Child Support Battles, and Manager Critiques Over Party Lifestyle

Teddy Sheringham: From Football Legend to Tabloid Fixture

Teddy Sheringham, 59, was a Premier League icon in the 90s and 00s, celebrated for his stints at Manchester United, Tottenham, and England. Yet, his off-field antics often stole headlines, painting him as football’s ultimate lothario.

[Image: Teddy celebrating the 1999 FA Cup win, caption: Teddy Sheringham’s career highs were often overshadowed by his off-pitch scandals.]

The Infamous ‘Dentist’s Chair’ Scandal
Ahead of Euro 1996, Teddy and teammate Paul Gascoigne sparked outrage during a boozy Hong Kong night. Photos showed them in the “Dentist’s Chair” drinking game, where alcohol is poured into reclining players’ mouths. Fans slammed their antics ahead of a major tournament, but manager Terry Venables shielded the squad, taking blame himself. Teddy later praised Venables’ loyalty: “He protected us, and we loved him for it.”

[Image: Teddy and Gascoigne in Hong Kong, caption: The 1996 ‘Dentist’s Chair’ incident became a symbol of England’s party culture.]

Romances and Scandals
Teddy’s love life made constant tabloid fodder. He dated glamour model Katie Price (then Jordan) in the late 90s, who claimed their split came when “he went cold” after media exposure. Later, his relationship with Miss Great Britain Danielle Lloyd, 17 years his junior, imploded post-Celebrity Big Brother (2007), where she faced racism allegations. Teddy dumped her publicly, partying hours after her eviction.

[Image: Teddy with Danielle Lloyd, caption: His romance with Danielle Lloyd ended amid reality TV controversy.]

Child Maintenance Battle
Teddy’s ex-partner Denise Sims accused him of neglecting their son Charlie, then 11, despite earning £22k weekly. In 1999, she revealed struggling on £125/week, living in a cramped Essex flat. Denise threatened court action, stating, “I want Teddy to pay for Charlie’s future.” Charlie later became a footballer, though their relationship remained strained.

[Image: Teddy with young Charlie, caption: Teddy faced public backlash over child support disputes.]

The Lonely Life of a WAG
Nicola Smith, Teddy’s girlfriend for eight years, warned others: “Don’t marry a footballer!” She described isolation and jealousy amid his fame, recalling girls “kissing Teddy in front of me.” Their 2001 split followed his flirtations in Portugal, which Nicola called “the final straw.”

Legal Troubles
In 2007, Teddy was arrested for allegedly dodging speeding fines by swapping points with West Ham teammates. Though charges were dropped, teammate Shaun Newton received a suspended sentence. Teddy denied wrongdoing, but the scandal added to his rebellious image.

Reformed Family Man
Since marrying Kristina Andriotis in 2016, Teddy embraced domestic life. They share two children and a home named Camp Nou after Barcelona’s stadium, where he scored in Man United’s 1999 Champions League win. Now a pundit and club ambassador, he’s swapped nightclubs for school runs.

[Image: Teddy with Kristina, caption: Teddy today: A devoted family man and media personality.]

Legacy
From “Dentist’s Chair” debauchery to reality TV stints (The Masked Singer, 2020), Sheringham’s journey mirrors football’s tabloid era. Yet, his redemption as a family man and respected analyst shows even the wildest stars can find calm after the storm.

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