Restructuring at Thomas Cook has taken its toll, as the holiday company's turnaround plan causes deeper losses.
The world's oldest travel company reported a statutory loss of £590m for the 12 months to the end of September - worse than the £518m loss recorded the previous year.
However, the firm's debt was reduced by £103m to £788m.
In 2011 the company was forced to request an emergency loan to avoid collapse.
Thomas Cook's new chief executive, Harriet Green, admitted the results represented "major issues" faced by the company last year, but insisted they masked improvement.
"Our brand has demonstrated its strength by recovering all the ground lost during last year's difficulties and we have identified significant further efficiency improvements," she said.
Trading towards the end of the summer was strong, the company said, adding that winter bookings were "off to a good start" in major markets.
The 171-year-old firm is in the process of reorganising its business and last year cut its fleet of planes to 35 and sold off 149 stores.
"The year ahead is the initial stage in this recovery and as we embark upon our first year of business transformation, we are optimistic about the future," Ms Green added.
The company's underlying loss - when one-off items are not included - narrowed from £103m to £37m in the year, but the group's revenue fell 3% to £9.49bn.
Shares in Thomas Cook fell more than 3% after the results were published.
More From Sky News