Jeffrey Epstein’s apparent suicide will renew scrutiny of his relationship with the Duke of York.

Here is a timeline of the controversy that has surrounded the pair:

– 1990s: The Duke of York is reportedly introduced to American financier Jeffrey Epstein through his friendship with Ghislaine Maxwell, the daughter of newspaper tycoon Robert Maxwell.

– 2000: Andrew and Ms Maxwell are seen on holiday with Epstein at Donald Trump’s Mar-a-Lago Club in Palm Beach, Florida. In return, the Duke reportedly invited Epstein to stay at Sandringham, Balmoral and Windsor Castle.

– 2001: Virginia Roberts claims to have had sex with Andrew “three times, including one orgy”, with the first encounter allegedly taking place in Ms Maxwell’s London townhouse. Ms Roberts claims to have had sex with Andrew on two more occasions – at Epstein’s New York home and at an “orgy” on his private island in the Caribbean.

– 2008: Epstein is sentenced to 18 months imprisonment after agreeing a plea bargain over child prostitution charges.

– 2011: Following Epstein’s release from prison, Andrew is photographed with him in New York. The Duke quits his role as UK trade envoy as a result.

The Duke of York has been embroiled in controversy over Jeffrey Epstein (Michel Euler/PA)

– January 2 2015: Buckingham Palace denies the Duke has committed any impropriety after he is named in US court documents related to Epstein. The woman, later named in reports as Ms Roberts, alleges in papers filed in Florida that she was forced to have sex with Andrew when she was 17, which is under the age of consent in the state.

– January 3: Buckingham Palace issues a second denial that the Duke had sexual contact with a woman who claims she was forced to have under-age sex with him, branding the allegations “false and without any foundation”.

– January 4: Andrew flies back to the UK from a ski resort in Verbier, Switzerland, following widespread reports of the under-age sex allegations facing him.

– January 13: The Duke of York’s ex-wife Sarah Ferguson defends him against “shockingly accusatory allegations” that he had sex with an under-age teenager, telling US TV show Today the family stood by the denial issued by Buckingham Palace.

– January 21: Lawyers for Ms Roberts formally request that he respond to her allegations under oath.

– January 22: The Duke publicly denies allegations he had sex with an under-age teenager in an address to guests at the World Economic Forum in Davos.

– July 7 2019: Epstein is arrested in New York on sex trafficking charges. Officials say the charges involve allegations that date to the early 2000s.

– July 12 2019: President Donald Trump’s Labour Secretary Alexander Acosta resigns following criticism of his handling of the 2008 plea deal with Epstein. Mr Acosta was the US attorney in Miami when he oversaw the non-prosecution agreement.

– August 9 2019: A US judge unseals legal documents which reveal Andrew was accused of touching the breast of “young college student” Johanna Sjoberg at Epstein’s home in 2001. The files relate to the defamation case that Virginia Roberts – now known as Virginia Giuffre – brought against Ms Maxwell in 2015. Buckingham Palace says the allegations are “categorically untrue”.

– August 10 2019: Epstein is reported to have been found dead from an apparent suicide at the Manhattan Correctional Center in New York. He was awaiting trial on sex trafficking charges.