Speaking with the BBC at the London Critics' Circle Film Awards Sunday night, Winslet, who co-starred with DiCaprio in 1997's Titanic and 2008's Revolutionary Road, said this year may be a winning year for the actor.
"I think you can sort of feel it, and I think that everyone wants it for him. It would be amazing," the Steve Jobs actress said of her longtime friend.
"It's also slightly difficult for me too, because Michael Fassbender has been nominated and I was his right hand woman for three months whilst we were making Steve Jobs and I saw how hard he worked. I think his performance is so extraordinary. But I think, yeah, you can sort of feel the temperature. It's probably going to be Leo's year."
As colleagues discuss DiCaprio's chances at winning the Oscar over the likes of fellow nominees Fassbender, Bryan Cranston, Matt Damon and Eddie Redmayne, the 41-year-old celebrity has been discussing his future roles.
Speaking with Germany's Welt am Sonntag, DiCaprio said he'd love to play Russian president Vladimir Putin, calling the role "very, very, very interesting."
"Lenin, too, would be an interesting film role," the actor continued, according to International Business Times. "I would play Rasputin too. I believe that there should be more movies about Russian history...Russia unites so many stories almost of Shakespearean character. For an actor, that's extremely exciting."
The two previously met in 2010 at a conference discussing protection of the Siberian tiger, where they spoke "only about the protection of these magnificent animals, not politics."