In 1999, after Manchester United’s iconic Treble victory, Dwight Yorke found himself celebrating in more ways than one.
The former United star, who played a key role in United’s success, found himself meeting someone rather special during the team’s pre-season tour in Australia.
That season had been legendary for Yorke, who scored 29 goals in 51 games, partnering with Andy Cole to help United win the Premier League, FA Cup, and Champions League. Yorke’s performances even earned him the Premier League golden boot, tied with Liverpool’s Michael Owen and Leeds’ Jimmy Floyd Hasselbaink.
However, it wasn’t just on the pitch where Yorke found success. A few months after that historic win, Yorke would have a memorable encounter with a Playboy model during United’s celebratory tour down under. In fact, Yorke later described the 1999 Australia trip as “one of the greatest I’ve ever undertaken.”
The summer tour was both a celebration and a series of money-raising friendlies for United, held at iconic venues like Melbourne Cricket Ground and Sydney’s Stadium Australia. With Sir Alex Ferguson back home receiving his knighthood, the team had assistant manager Steve McClaren in charge, who did his best to enforce curfews. But some players, Yorke included, enjoyed a bit of freedom.
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Yorke, now 52, recalls being “transfixed” upon meeting model Gabrielle Richens, also known as “the Pleasure Machine” after a steamy airline commercial. In a 2011 interview with FourFourTwo, Yorke called her “the most extraordinarily beautiful girl it has ever been my pleasure to know.”
He had actually been hoping to meet Gabrielle, who was already a well-known name in Australia thanks to her modeling career and her relationship with rugby star Solomon Haumono. With her striking looks and charm, she was Australia’s “It girl” at the time, even gracing the cover of Australian Playboy and posing for Black+White magazine.
After swapping numbers, Yorke and Gabrielle met up the next evening, defying curfew again. Yorke had to get creative to bring her back to his hotel, reportedly bribing the security guard with cash. “Listen, mate,” he recalled saying, “I’ve got Gabby coming up.”
When the guard asked, “Gabby who?” Yorke responded, “You know, the Pleasure Machine.” This seemed to do the trick, with the guard’s eyes nearly popping out in excitement. Yorke humorously remembered slipping the guard $100, saying he would have handed over a year’s bonus if necessary.
That night ended around 6 a.m., as Gabrielle left with the sun coming up. Yorke remembers it as a magical experience that made that trip to Australia unforgettable, a highlight of his life during a year that was already filled with extraordinary highs.
For Yorke, 1999 was a year of celebration both on and off the field, a time when success followed him everywhere—from winning trophies at Old Trafford to unforgettable encounters down under.
