In footage released Wednesday, Weinstein is seen hugging, touching and making suggestive comments during a business meeting in NY with Melissa Thompson.
At the start of the video, Weinstein rejects an effort by Thompson to shake hands, opting instead to give her a hug while rubbing her back.
"That's nice. Let's keep it up" he can be heard saying.
Dozens more women have accused him of sexual misconduct, assault, and rape.
Harvey Weinstein attends an event on October 5, 2011 in NY.
Melissa Thompson filmed the meeting with the Hollywood producer when she went to the Weinstein Company offices in NY in 2011.
Thompson told Sky News that she did feel she ever encouraged Weinstein's advances and felt that he was playing a game of "cat and mouse" with her to test her limits and identify her vulnerabilities.
That's where Thompson says Weinstein raped her.
Woodward book goes on sale as ex-Trump aides push back
This image released by Simon & Schuster shows " Fear: Trump in the White House ", by Bob Woodward , available on September 11. Both Mattis and Chief of Staff John Kelly have denied making any disparaging comments about the president.
"It is hot. You're hot", Weinstein replies. "Am I allowed to flirt with you?" he asks near the beginning of the meeting. Later footage shows Thompson re-adjusting the angle of her laptop so that she and Weinstein would remain on camera even as he beckoned her to a different part of the room.
Thompson told Sky News he then ran his hand up her skirt. "That's a little high". "That's a little high". "That's too high." However, the media mogul remained undeterred and kept stroking her arm, even claiming at one point that, "data is so hot, right".
"If I tried to fight myself away from him, he would more around to block me in somewhere and he's a big individual".
Thompson is clearly uncomfortable throughout the video, at one place telling Weinstein his hands were moving too far up her leg. Instead, Thompson said, he raped her.
After the meeting, she says, Weinstein arranged to meet her a few hours later at a hotel lobby, where she thought they were going to close the deal, according to Sky News.
As well as the civil suits, Weinstein also faces criminal charges - he has denied all allegations. His attorney Benjamin Brafman told Sky News that when viewed in its entirety, the video shows there is nothing forceful in Weinstein's actions. "This is a further attempt to publicly disgrace Mr Weinstein for financial gain and we will not stand for it. Facts do matter".
Thompson is among three women now suing the megaproducer for alleged sexual assault.
Out on $1 million bail after having plead not guilty to the first round of indictment and having surrendered his passport earlier this summer, Weinstein is set to be back in Justice Burke's Manhattan courtroom on September 20. They include: film actress Rose McGowan, who said Weinstein raped her in 1997 in Utah; "Sopranos" actress Annabella Sciorra, who said he raped her in her NY apartment in 1992; and the Norwegian actress Natassia Malthe, who said he attacked her in a London hotel room in 2008.