Gisele Bundchen The red carpet golden couple of the mid-Noughties, this gorgeous twosome dated from 2000 before they finally called it quits in 2005.
Naomi Campbell A whole twenty years ago, Naomi Campbell and Leonardo Di Caprio allegedly enjoyed a quick fling – it also widely summised (by us) that this is where his love of dating the world’s most beautiful and sought-after models, began.
Brunette beauty queen Helena was one of the original Victoria's Secret Angels and worked with the lingerie brand throughout the Nineties. Leonardo began dating Czech supermodel Eva Herzigova in 1998.
They tried to keep their month-long courtship under the radar as the Victoria's Secret muse was in the process of divorcing Bon Jovi drummer Tico Torres.
There seems to be no bad blood between them with Gisele telling Access Hollywood in 2009: "We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best." Gisele's relationship with Victoria's Secret lasted a tad longer - she was an Angel from 2000 until mid-2007.
Leonardo moved onto another identikit blonde lingerie model in 2005 in the form of Bar Refaeli.
The pair, who were just teenagers at the time, were caught "canoodling around New York", according to People Magazine.
Things reportedly ended after Bridget, who modelled for Victoria's Secret in 1998, found their "night of love" disappointing. Naomi, who made numerous appearance on the Victoria's Secret catwalk between 19, and Leo remain good friends.
She is a regular at his charity benefits and the pair often jet off on exotic holidays together.
The 41-year-old Hollywood actor has just hooked up with his TENTH - yep, that's a massive number 10 - Victoria's Secret model.
The Revenant star was spotted soaking up the sun with Danish beauty Nina Agdal in Malibu earlier this week, before the pair got down and dirty in the sand.