President Donald Trump said the reports were inaccurate.
The Times did not obtain Trump's tax returns, but someone who had legal access to the returns gave the newspaper information about their contents.
The losses, in the 1980s and 1990s, were greater than those reported by almost any other American taxpayer during that period, according to Internal Revenue Service data the Times said it had reviewed. The biggest losses occurred between 1990 and 1991 when Trump reportedly lost over $250,000 each year.
The New York Times reported that from 1985 to 1994, the president incurred a total of $1.17 billion in losses.
This is the most comprehensive look we've been able to glean of Trump's tax returns thus far, and it paints a picture of a failed businessman who conned the American people into thinking he was successful.
The newspaper said Trump posted losses in excess of US$250 million in both 1990 and 1991, which appeared to be more than double any other individual USA taxpayer in an annual IRS sampling of high-income earners.
During that period, Trump's debt-laden businesses, including casinos and hotels, struggled to survive.
Mr Trump's tax information shows he only paid taxes during two years during the decade the Times examined.
Released online last night with the alternate title "Decade in the Red: Trump Tax Figures Show Over $1 Billion in Business Losses", it's a rather breathtaking read.
US Treasury Secretary Steven Mnuchin in a letter to the House of Representatives Ways and Means Committee said Monday he would not release Donald Trump's tax returns as requested by the panel. He lost so much money, he did not pay income taxes in eight of those 10 years.
The NYT said it "was then able to find matching results in the IRS information on top earners - a publicly available database that each year comprises a one-third sampling of those taxpayers, with identifying details removed".
Trump said the Times story was based on "very old information" and a "highly inaccurate Fake News hit job!"