But he remains hopeful for a beautiful reconciliation.
Jimmy Kimmel, who has been engaged in an onscreen feud with the actor for more than a decade, is hosting the ceremony and had last week started the torture process early by leaving a little present on his seat.
"I don't know what he has in store for me," Damon told E! News' Ryan Seacrest on the red carpet, more than an hour before the start of the show. "It's going to probably be ugly."
Image Group LA/ABC via Getty Images
The feud began in the early days of Jimmy Kimmel Live!, which Kimmel began ending his shows by saying they had run out of time to interview Damon, even though he was not scheduled. Damon has played along over the years and has yet to make an official appearance as a traditional interview guest on the show. Will they make amends at the Oscars?
"We've tried a lot of couples therapy and that hasn't seemed to kind of cut through at all," Damon told Seacrest. "Maybe tonight's our night."
The actor noted that he at least will be able to made it inside the theater, seeing that he is a member of the Academy of Motion Pictures Arts and Sciences, which votes on the Oscar winners.
Manchester by the Sea, which Damon co-produced, is nominated for six Oscars, including Best Picture. If it wins the big prize, the actor would win his second Oscar and share the honor with four other people.
"One thing I know Matt Damon will not be throwing at me is an Oscar, because he's not gonna win," Kimmel joked on The Ellen DeGeneres Show last week. "Maybe he can throw tissues at me."
"We have a fire hose at the ready," he told E! News' Jason Kennedy last week. "If we have to, we'll use it."
For complete Oscars coverage, tune in to E! News at 7 p.m. and Fashion Police at 8 p.m. on Monday, Feb. 27.