Manchester United is considering a £600m bond issue in an effort to curb its debts.
JP Morgan, which orchestrated the club's £790m takeover by the American Glazer family in 2005, and Deutsche Bank are working with the club amid rising concerns about its debts, the Times reports.
Advisers are approaching potential investors on a bond issue to raise cash to aid repayment.
Manchester United owes about £700m to banks, financial institutions and hedge funds, according to debt specialists Capital Structure, mostly from the Glazer takeover.
The club insists the debt is not a problem as the annual interest on the loans is met by its operating profit. In 2008, net interest on all its debts was £69m against an operating profit of £72m.
The main concern for the club's owners is the £175m of loans the Americans are personally responsible for and which "roll up" interest at an annual rate of 14.25%.
Payment in kind (Pik) notes borrowed from US hedge funds Perry Capital and Citadel initially stood at £138m in 2006, but have since accrued £40m of unpaid interest.
If the club's financial performance falls below a certain level, the hedge funds have the right to appoint their own directors to the board.
Sources familiar with the situation say Manchester United will seek between £500m and £600m, more if investor appetite is strong.
The Glazers would prefer to use the money to pay back the more costly Pik debt, but experts say any attempt to prioritise the hedge funds would be met with stiff opposition from the club's senior bank lenders.
Instead, bankers say the club might look to pay off the bank debt, which is likely to have higher interest rates than the cost of the annual coupon on the bond.
Other big name clubs are also facing a cash crisis. Last week Chelsea owner Roman Abramovich converted £340m in interest-free loans into equity.
Regular reminders and updates
9 December 2019 deadline
Joe McDonnell joins as head of portfolio solutions (EMEA)
Adviser of the Year - South East
Fidelity Multi Asset CIO's outlook