Melissa Thompson, who has previously publicly complained of abusive behavior by Weinstein during a 2011 business meeting in New York, gave a tape of the encounter to Sky News.
Thompson told the station she had been offering her tech company's video platform to the 66-year-old, and recorded the meeting as part of the pitch.
Just hours later, Weinstein allegedly raped her in his hotel room, the woman told Sky News.
AFP reached out to Weinstein's lawyer Benjamin Brafman for comment but there was no immediate response.
He was quoted by US-based entertainment magazine People however as denying sexual misconduct by his client.
"Several respected journalists and trustworthy individuals have seen the entire video, as Ms. Thompson has been trying to promote it to for several months," Brafman's statement read, according to People.
"What they shared with us is that the video, when viewed in its entirety, in context and not in select excerpts, demonstrates that there is nothing forceful, but casual -- if not awkward -- flirting from both parties."
The former Hollywood titan is seen in the video waving staff away with the words "don't interrupt, don't interrupt' as he enters the meeting.
Thompson offers her hand but Weinstein goes in for a hug instead.
"That's nice. Let's keep it up. It's not bad," he says as he rubs her back.
"Am I allowed to flirt with you?" he is heard asking, and Thompson replies: "Um, we'll see, a little bit."
- Naivety -
At one point on the recording, Weinstein reaches under a table and appears to move his arm up her leg.
"Let me have a little part of you. Give it to me. It's okay, would you like to do it some more?" he can be heard saying.
"A little high, a little high, that's a little high, that's a little high," Thompson replies.
Weinstein has been accused by dozens of women of a litany of sexual misconduct ranging from harassment to rape.
He is out on bail and has pleaded not guilty in New York to six counts allegedly committed against three women in 2004, 2006 and 2013. The next hearing in the case is scheduled for September 20.
The allegations against the once-powerful movie mogul spurred the #MeToo movement that saw women worldwide speak up against sexual harassment and assault by men in powerful positions.
Thompson told Sky News Weinstein was "playing a cat-and-mouse game from the very beginning to see how far he could push me, and what my reactions might be so that he could gauge how he would play with (me), where my levers were, what were my vulnerabilities."
She is seen watching the footage along with a Sky News reporter, and denies encouraging him, telling the channel: "I think there was a combination of confidence and naivety that led me to this dynamic that we see now, watching back."
- 'Trapped' -
In the footage, Weinstein invites Thompson to join him at the Tribeca Grand Hotel lobby restaurant. She told Sky News she was expecting that this would be a follow-up meeting to close the deal.
"It wasn't an invitation to go to his hotel room. It was an invitation to come to a hotel lobby that was within blocks of the office and so that to me felt much safer than being alone with him in his office," she said.
When she arrived, Weinstein allegedly led her to his hotel room where she says he raped her.
"If I would try to fight myself away from him, he would then move around to a place where he could block me in," Thompson said.
"I constantly felt trapped, no matter where I turned. He cornered me, over and over again."
Thompson was part of a class action lawsuit against Weinstein filed in June in which she claimed the producer began to harass and fondle her, several US media outlets reported.
She reportedly claimed in court documents that Weinstein tried unsuccessfully to force her to perform oral sex on him before he pushed her on the bed and raped her.
But Brafman accused Thompson to trying to bolster her position in the lawsuit.
"Any suggestion of sexual misconduct is false. This is a further attempt to publicly disgrace Mr. Weinstein for financial gain, and we will not stand for it. Facts do matter," the lawyer told People magazine.
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