Re: Ash Vs. May, who really would've won?
Part of me wants to say May because well it is Fire vs. Grass, but then remember this is the anime and that means diddly-squat. Ash is the new Champion of the Battle Frontier and an accomplished trainer. I'd say if the writer's hadn't tied it off nicely with a draw Ash would've won.
Mind you May is more familiar with the Contest format and the point system, she also had a good chance. Quite a hard one to call, but at a push probably Ash.