He did not win anything besides the silver conference. and
the Orange league in Season 2
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Episode 268 is when the league starts
Ash has won a league, the Orange Island League, in season two of the anime.
If you are talking about after the Johto League tournament, yeah. They meet in episode 319. :D
Ash went there because he lose the Kanto League in the anime. Now, if you're talking about RED, that's other topic, as Ash has NEVER appeared in any main game.
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....