Gary Barlow and two other members of Take That have refused to comment on reports that they face having to pay tens of millions of pounds in tax after a court ruled a partnership in which they invested was a tax avoidance scheme.
Gary along with Howard Donald, Mark Owen and their manager Jonathan Wild invested £66 million into two-partnerships styled as music industry investment schemes, The Times reported.
Judge Colin Bishopp ruled that 51 partnerships set up by Icebreaker Management were to secure tax relief for members and HM Revenue and Customs is now expected to demand repayment.
In his ruling, the judge said: "The Icebreaker scheme is, and was known and understood by all concerned to be, a tax avoidance scheme.
"The aim was to secure sideways relief for the members, and to inflate the scale of the relief by unnecessary borrowing."
Almost 1,000 investors are understood to have placed at least £300 million in the scheme, The Times said.
It was alleged in 2012 that Gary, Howard, Mark and Wild invested at least £26 million in a scheme run by Icebreaker Management.
At the time Take That's lawyers insisted the bandmates believed the investments were legitimate enterprises and that all four named paid "significant tax", according to reports.
There has been no suggestion that fellow Take That bandmates Jason Orange and Robbie Williams were involved in the scheme.
A spokesman for Take That said there was no comment from Gary, Howard, Mark or Wild.
An Icebreaker Management spokesman said: "Icebreaker Management is extremely disappointed with this decision since it puts a valuable source of funding for the UK's independent music industry in jeopardy.
"Icebreaker will review the full decision and consider all the LLPs' options including appeal."
An HMRC spokesman said: "HMRC has put in place generous reliefs to support genuine business investment and our tax reliefs for the creative industries work well, enabling the UK's world-class film, television and video production companies to compete on the global stage.
"But we will not tolerate abuse of the system by people trying to dodge their tax obligations. HMRC will continue to challenge in the courts and anyone who engages in tax avoidance schemes risk not only the high cost of these schemes but also lay themselves open to penalties and, potentially, prosecution."
Martin Taylor, head of client relations at Rebus Group, said: "In light of recent first tier tribunal rulings and the proposed HMRC legislation, this ruling is yet another nail in the coffin for investors. The average investor in Icebreaker invested £357,266 and there are a couple of high net worth individuals who invested many millions of pounds.
"As a result of this decision and the legislation outlined in the Budget 2014, this will not only affect investors in Icebreaker, but will impact investors in any number of schemes believed to be similar, especially where they rely on being 'Active Members' irrespective of whether they are currently being investigated by HMRC.
"Subject only to appeal, members of the partnerships should expect to receive demands for repayment of any tax relief received in the immediate future."