Trump, who is running for US Presidency, made the claims during an interview in 1997 when he said that Diana was "crazy" but that he would still have slept with her.
The comments were made on Howard Stern's radio show, which the controversial businessman was a regular guest on.
Trump and Stern would often comment on how good looking famous women were, and one night the princess caught the eye of The Apprentice star.
Stern questioned him: "Why do people think it’s egotistical of you to say you could’ve gotten with Lady Di? You could’ve gotten her, right? You could’ve nailed her."
Trump replied: "I think I could have."
And in a interview in 2000, he asked Trump again whether he would have tried to woo Diana.
Stern asked: "Would you have slept with her?"
And the businessman replied: "Without even hesitation."
He told Stern he thinks he could have slept with her and described her as having "supermodel beauty."
Trump quipped: "She had the height, she had the beauty, she had the skin."
Last year, Selina Scott claimed Trump pursued Diana to the point of "stalking" her, saying he gave the late princess "the creeps".
Selina wrote in the Sunday Times: "He bombarded Diana at Kensington Palace with massive bouquets, each worth hundreds of pounds.
"Trump clearly saw Diana as the ultimate trophy wife. As the roses and orchids piled up at her apartment she became increasingly concerned about what she should do.
"It had begun to feel as if Trump was stalking her.
"When she died in the tragic accident in Paris in 1997 Trump told friends his biggest regret was that they hadn’t dated.
"He said that he always thought he had a chance of romance and would have had a 'shot' with her."
Earlier this week the election candidate claimed he would reverse the closure of Guantanamo Bay and "load it up with bad dudes" if he became President.
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