The previously undisclosed documents leaked to the newspaper relate to 1995 when Trump reported a $916m (£706m) loss across some of his business interests.
The revelations, which Trump's campaign did not confirm or deny, come amid growing calls for him to release details of his tax affairs, something all Presidential candidates have disclosed since 1976.
According to experts on tax consulted by the newspaper, the loss could have resulted in Trump not owing taxes for as long as 18 years due to a tax provision where losses would cancel out taxable income from other business and in other tax years, something which is perfectly legal.
“Mr Trump is a highly-skilled businessman who has a fiduciary responsibility to his business, his family and his employees to pay no more tax than legally required,” Trump's campaign said in a statement to the newspaper.
“That being said, Mr Trump has paid hundreds of millions of dollars in property taxes, sales and excise taxes, real estate taxes, city taxes, state taxes, employee taxes and federal taxes. Mr Trump knows the tax code far better than anyone who has ever run for President and he is the only one that knows how to fix it.”
In the first head-to-head debate between the two rival Presidential candidates, Hillary Clinton accused Trump of not paying federal income tax, to which he replied "that makes me smart".