Makes 0 sense, but that's not to say it wont happen.
If Olivera gets past Gathje, and he's beaten Tony, Chandler, Dustin, and Gathje in a row then asks for Conor, I can see them making it happen. Dana will just put it on the champ like he did with Bisping v Hendo, and GSP v Diaz. "He wants and he's earned the right to blah blah blah... " and you have a major event.
They've given title shots to guys coming off a loss before. Randy (Twice), Aldo (after 2 losses), Penn, Diaz, Eilers, Hendo (AS fight was semi legit because he was the lineal Pride MW champ), Chael, Edgar, and Tate. That's not counting instant rematches (which are mostly justified).