yep he did win it and got all the badges to show it
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The Semi Final Frontier
he goes to a another battle frontier.
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....
Ash leaves Hoenn (Battle Frontier) in episode 468: Home Is Where The Start Is and arrives in Sinnoh in episode 469: Following A Maiden Voyage.
Yes, May returns during the Sinnoh season for the Wallace Cup competition where she meets up with Ash and Brock again.