Jury selection is scheduled to start this week, with the 67-year-old facing charges of predatory sexual assault, a criminal sexual act and rape. He denies all charges and has pleaded not guilty.
Since the allegations against Mr Weinstein were first revealed by the New York Times in 2017, helping to launch the #MeToo movement, more than 75 women have come forward to accuse the American of sexual misconduct ranging from harassment to assault.
Many of these women are expected to attend the hearings, which are being held at New York’s Supreme Court.
The case against Mr Weinstein centres on the charge that he raped a woman, who has not been identified, at a New York hotel in March 2013, and the allegation he forced a production assistant into a sex act at his Manhattan apartment in 2006.
If he is convicted of the most serious charges against him – two counts of predatory sexual assault – the disgraced businessman faces a mandatory life sentence.
For that to happen, prosecutors must demonstrate Mr Weinstein had a habit of violating women. They plan to call upon actress Annabella Sciorra, who says the movie mogul forced himself inside her Manhattan apartment in 1993 or 1994 and raped her after she starred in a film for his movie studio.
Other accusers, whose allegations have not been brought to trial, will be permitted to take the stand as witnesses to illustrate an alleged pattern of abusive behaviour.
Publicly, Mr Weinstein has largely ignored the allegations made against him but last December complained that his “work has been forgotten”.
“I made more movies directed by women and about women than any film-maker and I’m talking about 30 years ago,” he said in the New York Post. “I’m not talking about now when it’s vogue. I did it first. I pioneered it.”
More recently, the American told CNN that the “past two years have been gruelling and have presented me with a great opportunity for self-reflection”.
In a joint statement released through Time’s Up, 25 of Mr Weinstein’s accusers addressed the significance of the upcoming trial, which is expected to run for two months.
“This trial is critical to show that predators everywhere will be held accountable and that speaking up can bring about real change,” their statement read in part. “We refused to be silenced and will continue to speak out until this unrepentant abuser is brought to justice.”
Mr Weinstein’s lawyer, Donna Rotunno, has argued the case is weak and said she plans to aggressively cross-examine the accusers. She added that her client would be “the first one to say he did bad things,” but that he is not a criminal.
Picking a jury for the trial is expected to be a difficult process, in part because immense media attention on the case could mean some potential jurors have already made up their minds. Mr Weinstein’s legal team attempted to get the trial moved out of Manhattan, but a court rejected that.