Prince Andrew took a previously undisclosed flight on Jeffrey Epstein’s private jet with a group that included a Russian model.

Andrew and Anna Malova, then 27, were among nine people on Epstein’s plane for a trip from the US Virgin Islands to Florida in February 1999, according to flight logs.

Malova was later jailed in the US for failing to comply with a court-ordered programme relating to her use of prescription painkillers.

The discovery of the flight added to pressure on Andrew over his friendship with Epstein, who this month was found dead at 66 in his New York jail cell while awaiting trial for sex trafficking. The city medical examiner ruled the death a suicide.

Andrew has vehemently denied any wrongdoing. He said in a statement on Saturday that he did not “see, witness or suspect any behaviour of the sort” that led to Epstein’s 2008 conviction for soliciting sex from an underage girl.

The prince said it was a mistake to have continued seeing Epstein after that.

The February 1999 flight, first reported by the Sunday Times, was recorded in logs kept by Epstein’s pilots that were filed to a US court by Virginia Roberts Giuffre, who has alleged she was used as a sex slave by Epstein.

The flight log was among almost 2,000 pages of records released by a federal judge in New York this month. It was missing from the notorious 73 pages of previously released Epstein flight logs, some of which also named Andrew as a passenger.

The group flew from St Thomas, the airport closest to Epstein’s private island, Little St James, to Palm Beach in Florida, where Epstein had a mansion. The disgraced money manager is accused of abusing underage girls at both properties and other sites.

There is no suggestion Malova or Andrew were involved in any wrongdoing during the trip.

They and Epstein were joined on the flight by others including Epstein’s close friend Ghislaine Maxwell, a daughter of the late financier Robert Maxwell who has been accused by several victims of assisting Epstein’s abuse of girls. Maxwell denies this.

Also present was Gwendolyn Beck, a former financial industry executive and friend of Epstein, who made a failed run for Congress in Virginia in 2014. Epstein donated more than $12,000 to Beck’s campaign.

Malova did not respond to an email. A former Miss Russia, she moved to the US and made it to the final of the 1998 Miss Universe beauty pageant, which was then owned by Donald Trump – another former friend of Epstein.

In 2010 she was accused of forging a prescription for Vicodin from a stolen doctor’s pad. She was jailed in May 2011 after repeatedly arriving late for a court-mandated drug programme. She denied all the charges against her.

Last week it was alleged that Andrew was once seen receiving a foot massage from “two young well-dressed Russian women” at Epstein’s home in Manhattan. The claim was made in an email by the literary agent John Brockman, another former Epstein associate.

Last week also saw the release of video of Andrew at Epstein's New York City home in 2010.