New pictures show Prince Andrew alongside Jeffery Epstein and 'madam' Ghislaine Maxwell at the Ascot races.
The never-before-seen photos of the scandal-hit royal were shown on the BBC program Panorama where Virginia Roberts shared new details of the night she allegedly had sex with Prince Andrew, claiming she felt "ashamed" afterwards.
In the photos, the trio are wearing hats and fancy racewear, laughing and smiling at the famous event in 2000.
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Another woman in pink is walking in front of them and appears to be chatting to Prince Andrew.
Ms Maxwell is the daughter of disgraced media tycoon Robert Maxwell and has long been accused of playing a key role in finding underage victims for Epstein.
The 57-year-old, who has constantly denied the allegations, hasn't been seen in public since around the time of Epstein's death.
Epstein was found dead in his cell at the Metropolitan Correctional Centre in New York City on August 10 where he was awaiting trial on child sex trafficking charges.
His death was ruled a suicide.
In 2005, police in Palm Beach, Florida, began investigating Epstein after a parent complained that he had sexually abused her 14-year-old daughter.
Epstein pleaded guilty and was convicted in 2008 by a Florida state court of procuring an underage girl for prostitution and of soliciting a prostitute.
The trio's outing at Ascot was at a time when the prince has claimed he was seeing Epstein once or twice a year.
Prince Andrew had been introduced to Epstein just months before by Ms Maxwell.
It was also during this time that Ms Maxwell and Epstein attended Windsor Castle for the prince's 40th birthday.
The Dance of the Decades, a lavish party hosted by the Queen, celebrated four royal birthdays, including Prince Andrew's 40th, the Princess Royal's 50th, the Queen Mother's 100th and Princess Margaret's 70th.
In Prince Andrew's interview with Newsnight last month he said Epstein was there at his invitation, not the royal family's.
He added that the financier was Ms Maxwell's "plus one".
Early the following year, in the most infamous photo of all, the Duke of York was pictured with his arm around the waist of 17-year-old Ms Giuffre, then known as Virginia Roberts, with Ms Maxwell stood in the background.
On the Panorama program Ms Giuffre, now a married mum-of-three, described sex with the Duke as "quick and disgusting".
"He got up and he said 'thanks' and walked out and I just sat there in bed, just horrified and ashamed and felt dirty and had to get up and have a shower," she said.
The interview was filmed before Prince Andrew's trainwreck BBC appearance last month, but the reporter confirmed Ms Giuffre stood by every word.
Ms Giuffre, 36, alleges she was trafficked as a sex slave by Epstein and made to have sex with Prince Andrew three times in 2001 and 2002, in the US, London and the Caribbean, when she was 17 years old.
Prince Andrew, 59, has vehemently denied he had sex with her and said he had no recollection of meeting her in a world-first interview with Newsnight last month.
Ms Giuffre, who now lives a low-key life in Cairns with her Australian husband and three children, said both she and Prince Andrew "know what happened".