While speaking on Today's show, Damon shared that he has been racking his brain wondering if he could have stopped Weinstein from doing such disgraced conduct.
The 47-year-old actor noted, "I've been reading these stories because I am racking my brain. Did I see something? Could I have known something? Is there something I could've done?"
Adding, "I don't know what I would've done."
Damon's history with the shamed Hollywood producer goes back decades, as it was Weinstein who put the actor's 1997 drama "Good Will Hunting" into motion.
They worked on numerous films together, but Damon claimed earlier this month that he "never" saw any of Weinstein's alleged behavior.
Earlier this week, during an interview to 'Good Morning America', Damon shared, "I knew the story about Gwyneth [Paltrow] [being sexually harassed by him] from Ben Affleck, because he was with her after Brad [Pitt]. I never talked to Gwyneth about it. Ben told me. I knew that they had come to whatever agreement or understanding, she was the first lady of Miramax. He treated her incredibly respectfully. Always."
Paltrow is one of over 40 women who have accused Weinstein of sexual harassment or sexual assault in a scandal spanning three decades.