The ex-Tottenham star, who managed to play professionally until he was 41, enjoyed a New Year sunshine break in Mauritius with stunning Kristina Andriotis, who at 23 his 20 years his junior.
Sheringham, who has dated a string of younger women over the years, including Katie Price and Danielle Lloyd, looks to be getting serious with his latest catch though.
Leggy: Kristina ties up her hair before taking a dip as Teddy Sheringham relaxes on a sun lounger in Mauritius
Kristina, a former model, is understood to have moved in with the sportsman last summer.
It begs the question whether Sheringham, father to 21-year-old Bishop's Stortford striker Charlie, could have been tamed from his womanising ways.
The flame-haired twin, who now works in PR, showed off her sculpted figure in a yellow bikini - and he didn't look too bad either.
Shapely coule: Teddy and Kristina head to the pool at their hotel
Kristian showed off her leggy figure as she stood up to tied her hair before the couple headed to the swimming pool and on their return Sheringham planted a kiss on her forehead as they shared a tender moment.
It's not he first time Sheringham and Kristina have been spotted together, as she used to be a regular on the party circuit.
Tender moment: Former England star plants a kiss on former model's forehead
They were pictured together back in 2007, but Sheringham has had plenty of company since then.
However, it seems the popular goalscorer couldn't get enough of a good thing and has opted out of life in the fast lane.
