Football’s 10 Biggest Playboys

george best

With all the money and fame that being a superstar footballer brings, it is not exactly difficult for the modern player to find a woman. But as the following list of football’s biggest playboys shows, sometimes one is not enough. Indeed, in some cases, sometimes 100 is not enough.

George Best

There is no-one who better epitomises the phrase “playboy footballer” than the late, great George Best. An absolute genius on the pitch with his dribbling skills and a whirlwind of a character off it, Best’s reputation as a lover of both women and alcohol was as much a feature of his career as his thrilling performances for Manchester United. His addictive personality would eventually contribute to his death but it’s best to enjoy the more light-hearted moments that came with his lifestyle: reported half-time rendezvous’ with various women, the dating of no less than four Miss World contestents and the classic quote “If I’d been ugly, you’d never have heard of Pele”.


Before George Best there was Garrincha, the disastrously-raised but ridiculously-gifted Brazilian footballer who had as much influence as Pele in helping his nation win the 1958 and 1962 World Cups. Born into a poverty-stricken family with a deformed spine and one leg two inches shorter than the other, Garrincha’s rise in world football was nothing short of inspirational. However with the rise to fame came some real horror stories: Garrincha was an alcoholic at 14, bizarrely lost his virginity to a goat, and fathered 14 children to numerous women. He was never able to overcome his off-field problems but Garrincha’s on-the-pitch performances mean he will always be remembered fondly by the Brazilian people, unlike media suck-up Pele.

Cristiano Ronaldo

Cristiano Ronaldo is one of the most well-known footballing players in the modern game. He’s wealthy, he’s famous, he’s a remarkably-talented footballer and he looks just a little better than Lionel Messi. His list of ex-lovers is so long that we complied a list of Cristiano Ronaldo’s ‘known’ girlfriends, and after 30 hot celebrities we’re still adding to it. That his mother had to come out and claim that Cristiano Ronaldo is no womanizer shows you just how bad (or good, depending on who you are) things have gotten.


The original, fatter Ronaldo may have scored an untouchable 15 World Cup goals for Brazil, but he made a faux pas of epic proportions when picking up a couple of hookers that turned out to be transvestites. To his credit he got out of there pretty quickly when he realised the mistake he had made, even paying the hookers for their time, but by that point the damage had been done as one of the transvestites, Andrea Albertino, tried to blackmail Ronaldo to keep his mouth shut. Ronaldo admirably refused, came clean on what he called the “worst decision of his life” and the footballing world chuckled at the unfortunate nature of it all.

Dwight Yorke

If having a child with Page 3 model Jordan was enough to have Dwight Yorke labeled a playboy footballer, his alcohol-fueled video session with Manchester United teammate Mark Bosnich took things a significant step further. Yorke has always enjoyed his success as a footballer to the fullest, still covering himself in bling at the age of 38, but the former Trinidad and Tobago captain’s decision to videotape himself and coke-sniffer Bosnich wearing womens clothing and partying at home with four lovely ladies took things just a little too far.

Antonio Cassano

Before he released his autobiography ‘La Dico Tutto’ (‘I’ll Tell You Everything’) Antonio Cassano was known as a brilliant Italian attacker with an extremely troublesome personality. Afterwards, he was known as a brilliant Italian attacker with an extremely troublesome personality who had bedded a lot of women. Indeed, if his book is to be believed then in the eleven years prior to the release date Cassano had slept with between 600 and 700 women, stating that he felt having sex on the day of a game enhanced his performance immensely. Sex and three or four post-sex Italian pastries, apparently.

Ashley Cole

Cheryl Cole is a very forgiving young lady. Husband Ashley Cole was a regular fixture in the Sunday tabloids with tales of him happily playing away from home, pausing only to vomit, and he seemed to somehow earn forgiveness every time. Which is a key chapter in the playboy playbook. However, the naked pics he sent to a glamour model’s phone in Februay 2010 proved proved to be the pixelated straw that broke the camel’s back, and the Coles were soon divorced with Cheryl citing “unreasonable behavior”.


Ronaldinho has been partying his career down the toilet since 2005, going from undisputed best player in the world to also-ran at Milan. One of the reasons for ‘Dinho’s decline is thought to be his extravagant disco schedule, which leads to many many meetings with ladies. One lap-dancer Ronaldinho met in 2002 described him as “not the best looking man I’ve ever been with” but “like a pneumatic drill” and “human Viagra”.

Frank Worthington

Football star’s personal lives didn’t fill newspapers in the 1970s as they do now, so you had to be pretty prolific to earn a playboy reputation. Frank Worthington still managed it. Worthington played for Huddersfield, Leicester, Bolton, Birmingham, Leeds, Sunderland, Southampton and many more. But he very nearly signed for Liverpool in 1972, only to fail the medical due to high blood pressure brought on by excessive sexual activity. If that’s not enough to convince you, then Worthington titled his autobiography “One Hump or Two?”

Gabby Agbonlahor

In 2008, Aston Villa striker Agbonlahor managed to match his on-field potency with his off. Agbonlahor started the season by scoring a seven minute hat-trick for Aston Villa, and just a couple of weeks later it was revealed that not only had he been juggling three girlfriends at once, he had also managed to get all three of them pregnant. Rumour has it that Agbonlahor is a very strong swimmer.

These are just some of football’s playboys but there are plenty more out there. Let us know some more in the comments.

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