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have a dangon , fire , dark,ice,poison type Pokemon
By beating the elite for then Beating the champion.
Ash has won a league, the Orange Island League, in season two of the anime.
I have the strong feelin that Ash will win this one because in the flow of pokemon history Ash becomes closer and closer to become a champion and in the sinnoh league, he is in the top 4 and i think in unova, in the finals Ash will battle Trip and Ash will win against him and become the winner and after that he will proceed in battling the elite 4 in different kinds of regions and enter the "Champions League" where champions in different regions battle in order to win and face the Pokemon Master and Ash will battle the Pokemon Master and then claim the title....
no one has won it yet,but ash has been knocked out unfortunately,in the future he might actually win a cup