Documents spanning two decades revealed two $750 (£582) income tax payments made as he campaigned in 2016, and again when he entered the White House in 2017, but otherwise none for almost a decade.
Mr Trump, who denied the report on Sunday night as “totally fake”, is said to have avoided paying any income taxes whatsoever for 10 of the previous 15 years, having argued that he lost more money than he made.
The NYT report did not include details of his personal tax returns for 2018 or 2019.
Despite reporting hundreds of millions of dollars in income over two decades, Mr Trump almost erased his tax bills by reporting heavy losses across his businesses – all the while spending on loss-making investments.
But, having used substantial amounts of that cash in the following years – much of it spent on loss-making golf courses across the world – the president’s cashflow was described as now being in bad health.
That included deals connected to his personal brand as well as the television show “The Apprentice,” which were alleged to have raised about $427.4 million (£333 million) for the future president altogether, according to the NYT analysis.
His golf resort near Miami, the Trump National Doral, was said to have been the source of most of his $315 million (£245m) losses from golf courses since 2000, whilst the Trump International Hotel in Washington DC recorded over $55 million (£42m) in losses since it opened in 2016.
The same year, the Republican presidential candidate had asked reporters why anybody would want to see his tax returns, telling the Associated Press there was “nothing to learn from them”.
In spite of that claim, the NYT report also revealed how Mr Trump has feuded with the Internal Revenue Service (IRS) for almost a decade over a nearly $73 million (£57m) tax refund he previously claimed.
If the IRS were to rule against him, Mr Trump could soon be responsible for paying over $100 million (£78m) to the federal government.
According to the NYT, the president will also become personally liable for paying-back more than $300 million (£234m) in loans in the next four years.
“It’s fake news. Totally fake news. Made up,” Mr Trump said, without addressing any of the story’s specifics or providing evidence to support his denials.
“Actually, I paid tax and you will see that as soon as my tax returns … they are under audit,” the president added, repeating a common refrain he uses to explain why he has not released his financial files, a customary step taken by every major-party presidential candidate for decades.
Should he lose the presidential election to Joe Biden in 36 days time, Mr Trump will likely face further scrutiny about his financial records as well as any conflicts of interest seen throughout his time in office.
Commenting on Sunday night’s revelations, Democratic congresswoman Alexandria Ocasio-Cortez accused the president of abiding by his own set of rules, writing on Twitter that he was a “walking scam”.
“[He] contributed less to funding our communities than waitresses & undocumented immigrants,” Ms Ocasio-Cortex wrote.
Democratic House speaker, Nancy Pelosi, added that Mr Trump had been shown to disdain Americans with his apparent tax avoidance over two decades.
“It is a sign of President Trump’s disdain for America’s working families that he has spent years abusing the tax code while passing a GOP Tax Scam for the rich that gives 83 per cent of the benefits to the wealthiest one percent,” she said in a statement.
The president’s election rival, Joe Biden, has yet to officially respond to the NYT revelations.