The footage, which has never been broadcast before, shows him hugging, touching and making sexually suggestive comments to 28-year-old Melissa Thompson.
Ms Thompson was at The Weinstein Company offices in New York in September 2011 to pitch her tech start-up company’s new video and analytics service.
As part of the demo, she recorded the meeting.
A few hours afterwards, at a hotel nearby, Ms Thompson alleges that Weinstein raped her.
Weinstein denies all non-consensual sexual contact.
In an interview, Ms Thompson told Sky News that initially she arrived at The Weinstein Company offices expecting a meeting with the marketing team.
Instead, the video shows Weinstein arriving alone, saying ‘don’t interrupt’ to nearby staff, shutting the door, and locking it.
Ms Thompson offers a handshake, Weinstein pushes her hand out of the way and hugs her, running his hands up and down her back and murmuring “that’s nice, let’s keep it up”.
Weinstein sits down and asks: “So am I allowed to flirt with you?”
Ms Thompson replies: “Ummm we’ll see, a little bit.”
At times Weinstein appears impressed with and interested in the product, and they discuss its capabilities and applications in some detail.
He says: “Wow. Okay, I’m going to use your service… on Marilyn Monroe, and then you know you can sign me up, tell your boss.”
As Ms Thompson showed the video to Sky News, she said: “Now I see he’s trying, in any way he can, to move me into that zone of comfortable then uncomfortable and confused, and vulnerable, and recognising that he’s powerful and I’m not, and that I need this deal from him, and he has the power to give it to me.
“I think (he) 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 me; where my levers where, what were my vulnerabilities.”
At points in the video Ms Thompson appears flustered, and loses her train of thought as she tries to continue her pitch.
There are also exchanges when she engages with Weinstein, leans towards him, touches or play punches his shoulder and arm, and responds to questions about her personal life.
During one interaction they are talking about the video platform and Ms Thompson says to Weinstein: “Data’s so hot right?”
Weinstein replies: “It is hot. You’re hot.”
He reaches down under the table, out of view of the camera, where Melissa says he ran his hand up her leg under her dress.
On the video he says: “Let me have a little part of you. Give it to me. It’s okay, would you like to do it some more?
She replies: “A little bit… a little high, that’s a little high, that’s a little high.”
Sky News asked Melissa if she thought she could have been encouraging his behaviour or flirting with him.
She said: “I don’t think I purposely encouraged him.
“I think there was a combination of confidence and naivety that led me to this dynamic that we see now, watching back.
“At first I tried to volley a little bit with him. If he made a comment, I would try to catch it and return it in a way that felt a little safer than the way he threw it at me.
“I was trying to save face a bit … trying to manage the situation.
“I didn’t want to blow the meeting.
“I worked in Wall Street before I went to business school, and I worked in an environment that was heavily male dominated… I thought I could handle it, I had never met anyone that I couldn’t handle… until Harvey Weinstein.”
At the end of the meeting Weinstein makes arrangements with Ms Thompson to meet in the Tribeca Grand Hotel lobby restaurant.
In an interview, she described how she was under the impression that meeting was to potentially close the deal.
She said: “It wasn’t at 10pm, 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.”
Ms Thompson said Weinstein came to the hotel lobby and told her to follow him.
She assumed they were going to a conference room, but it was Weinstein’s hotel room.
There, she said, he raped her.
She said: “If I would try to fight myself away from him, he would then move around to a place where he could block me in. I constantly felt trapped, no matter where I turned. He corned me, over and over again.”
The recorded meeting and the alleged rape are both included in a class action lawsuit against Weinstein and others connected to him who might have known what was happening.
Ms Thompson said: “Had people been more vocal and not said ‘yeah that’s Harvey or yeah you have to live with that’… you don’t.
“We don’t have to live with things that are illegal and abusive.
“We don’t have to live with being raped when we think we are going to a business meeting.”
In a statement Harvey Weinstein’s lawyer Benjamin Brafman said: “Several respected journalists and trustworthy individuals have seen the entire video.
“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.
“Anything short of that is intended to make Mr Weinstein appear inappropriate, and even exploitative.
“It was produced by Ms Thompson to bolster her position in a civil lawsuit seeking money.
“This is a further attempt to publicly disgrace Mr Weinstein for financial gain, and we will not stand for it.
“Facts do matter.”
Sky News has not paid Ms Thompson for the video, nor did she request it.
Dozens of women have accused Weinstein of harassment and assault.
As well as the civil suits, he also faces criminal charges.
Weinstein has consistently denied all allegations of non-consensual sexual contact.