14 January,2013 09:39 AM IST | | AFP
The English newspaper - which in December announced it was suing Armstrong for over £1 million ($1.6 million, 1.2 million euros) over a libel payment made to him in 2006 - picked the Chicago Tribune as it is in the city where Winfrey hosts her show on her OWN cable TV network to be broadcast on Thursday.
Among the questions asked are whether Armstrong told doctors in 1996 that he had used EPO, human growth hormone, cortisone, steroids and testosterone, whether he intends to return his prize money, and whether he accepts "lying to the cancer community was the greatest deception of all".
The crux of the matter is whether Armstrong, having been stripped of his seven Tour de France titles, will finally admit that he was a drugs cheat. Such a confession would overturn more than a decade of strenuous denials.
There is also a potential threat to Armstrong's liberty, stemming from the fallen icon's role in the US Postal Service team, where he spent his most successful years in the saddle.
He could also be accused of perjury over disclosures made under oath to a US federal jury in 2005. If convicted, each false statement could lead to five years in jail.
Armstrong has always maintained that he did not use banned substances during his stellar career, but in August last year he chose not to contest charges put forward by the US Anti-Doping Agency (USADA) that he was a serial drugs cheat.
The Sunday Times was one of the few publications to openly query Armstrong's innocence during his career. The paper had to pay Armstrong £300,000 ($480,000 US, 362,000 Euros) to settle a libel case after previously suggesting that he may have cheated.
The Sunday Times is reportedly demanding the return of the original settlement payment, along with interest and legal costs.
The newspaper had long questioned Armstrong's achievements and in 2004 it published an article stating that it was appropriate for questions about his success to be "posed and answered".