The 67-year-old, once one of the most powerful figures in Hollywood, is facing five charges of rape and sexual assault involving two women.
The trial at New York's Supreme Court – which is set to take place over a two-month period – is expected to be the focus of intense media scrutiny.
Dozens of high-profile women, including actresses Gwyneth Paltrow and Angelina Jolie, have made allegations of sexual abuse and harassment against Weinstein since the publication of revelations in the New York Times in October 2017.
He has denied any non-consensual sex and will plead not guilty.
Weinstein was originally accused back in October 2017 when an in-depth investigative article by The New York Times was published which noted the stories of several women who came forward with accusations of sexual harassment regarding the Hollywood producer.
It was this case that catapulted the #MeToo movement and Time's Up campaigns to support the victims of sexual misconduct.
The Miramax co-founder was indicted in May 2018, on charges of rape in the first and third degrees and first-degree criminal sexual act.
He has denied all allegations of non-consensual sex and remains free after posting $1 million bail.
If convicted, he could face a life sentence.
In a previous interview, the disgraced movie mogul told The Spectator: “You were born rich and privileged and you were handsome. I was born poor, ugly, Jewish and had to fight all my life to get somewhere. You got lotsa girls, no girl looked at me until I made it big in Hollywood.”
He continued: “Yes, I did offer them acting jobs in exchange for sex, but so did and still does everyone. But I never, ever forced myself on a single woman.”
Rose McGowan, a Hollywood actress who is one of 80 women who claims that they were abused by Weinstein, refuted his statements on Twitter.
"Rapists are liars," she wrote, followed by a second tweet claiming that his quotes do not make logistical sense.
Being that I was in the middle of my second film for his company, having NEVER met him before the morning of my rape, and never worked for him again, this is a clear lie. Nice try, rapist. https://t.co/A2l3U1Wp4h— rose mcgowan (@rosemcgowan) July 13, 2018
Per the deal, his accusers — along with potential claimants who could join in coming months — would share in the payout.
The deal would also bring to an end nearly every such lawsuit against him and his former company.
A number of parties involved in legal proceedings have expressed disdain at the tentative deal.
"This settlement breaks my heart," Zoë Brock, a model who was one of the first women to accuse Weinstein of sexual misconduct, said in a statement.
"I have signed it only because I have explored every other legal option and at this point have found no alternative," Brock said, adding: "Let us hope the criminal system does not go as easy on Harvey as the civil system has."
The former Weinstein Company boss recently spoke with the New York Post, making the claim that he actually did a lot more for women in cinema than he has been given credit for.
"I feel like the forgotten man," he said.
"I made more movies directed by women and about women than any filmmaker, and I’m talking about 30 years ago. I’m not talking about now when it’s vogue. I did it first! I pioneered it!
"It all got eviscerated because of what happened. My work has been forgotten."
Weinstein conducted the interview in a medical clinic following spinal surgery. At one point, he hailed The Weinstein Company for its purportedly progressive nature, stating:
"This was a company that took social issues and tackled them."
Weinstein also highlighted his charity work and threatened to shut the interview down whenever a question that he didn't approve of was fielded.
“I want this city to recognise who I was instead of what I’ve become," he lamented.