Plus there was the Chimchar incident that the writers thought to give Ash the win due to that. So I think it was fair compared to the Whirl Cup crap.
Torchic vs Tailow in the mob episode. But we all knew Ash was better than May because he was whooping trainers left and right from start of the episode to finish. Losing one match doesn't determine the strength of his whole team.May won against Ash in early AG? When?