He might. I think not because of with all of the other bosses he didnt battle.
Giovanni was the gym leader and Ash didn't even battle him. And Cyrus isn't a gym leader, so most likely no.
I'm not sure, but I'd guess that he will. This season is more like the games than any other in many respects, and anyway look at Paul. Ash only fought Gary twice IIRC, near the beginning and end of Johto. But he's faced Paul many times already, so perhaps they'll change the 'big, bad boss' also, and have him face Ash, at least once. I know I'd like that.
he never battled with giovanni,
but idk