Fairfax Media losses ballooned to $2.7 billion as the media company took a major write-down as part of its corporate overhaul.
The net loss, which included a non-cash impairment charge of $2.79 billion, follows a loss of $390 million for the year earlier, the company said.
Earnings before interest, tax, depreciation and amortisation totalled $506 million in the year to June 30, down 16.7 per cent.
Fairfax shares fell as much as 2 cents, or 3.5 per cent, in early trade to 54.5 cents.
The company, publisher of this website, said that after the latest write-downs, net assets of Fairfax would remain in excess of $2 billion.
"The cyclical downturn worsened during the 2012 financial year, while continuing structural change is affecting our Metro Media division," said Fairfax Media chief Greg Hywood. "We continue to drive significant change through the business, consistent with our strategy, and we are responding to a stressed economic environment."
In June, Fairfax announced that 1900 staff - approximately one in five - would be cut in a major shake-up of the company.
Fairfax also said it would introduce pay-walls for its websites and shrink the print format of its two major metro papers, The Sydney Morning Herald and The Age. The restructure of the business is aimed at aligning the company with readers’ shift to digital news, a trend that is reshaping the media industry globally.
The company said it expected generate annual savings of $235 million by 2015 through the changes.
Since then, Fairfax’s biggest shareholder, mining magnate Gina Rinehart has stepped up pressure on the company by seeking as many as three board member seats, and criticised the board's leadership.