Manchester United's owners made a £108.9million loss last year, according to their latest set of accounts.
The loss by Red Football Joint Venture, the Glazer family's parent company that owns United, include some one-off costs from setting up the £526million bond scheme last year to replace their bank loans, according to accounts filed at Companies House.
The lack of income from selling players also contributed to the loss for the year ending June 30, 2010 - the previous year the company had recorded £21million profit thanks largely to the £80million sale of Cristiano Ronaldo.
Last year's losses included £30.2million interest on their £220million payment in kind (PIK) loans which have since been paid off.
United's club accounts were published in October and revealed losses of £83.6million - the PIK interest payment is not included in the club accounts - but club chief executive David Gill said then there was £165million in the club's bank account and that they were in a healthy position.
Gill said in October: "We have money in the bank so there is zero pressure on that, no pressure at all to sell any star player.
"The philosophy is to retain and attract the best players. We have £165million in the bank but in some ways we would prefer to have £80million in the bank and Ronaldo on the pitch."
The highest loss recorded by a Premier League club was Chelsea's £132million in 2005.