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Diantha already showed all her strategies, so Leon already has a way to counter everything she could do. She always prepares his party in advance to face his opponents, so it makes perfect sense that his battles always end in sweeps.
What makes Ash such a difficult opponent for Leon is that he doesn't have strategies, he comes up with shit right on the spot, so there's no way to counter him. Ash's out of the box thinking will give him the victory against Leon
