The problem for Matt Damon is that he mostly isn't a showy actor. Actors like him that are more subtle are always getting overlooked for awards.
He has deserved several nominations for acting and it sucks that his second acting nomination was for Invictus. He should have gotten in for The Informant instead in Best Actor, but that wasn't happening.
It's also possible Damon will direct one day or at least write another script for someone else to direct. I could actually see Affleck directing a script him and Matt write.