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Uhm... personally, I DO think they will let us know if she won or not. But that will not bring her back. I mean, they show Misty in every Kanto reunion because SHE IS FROM KANTO. May on the other side, is from Hoenn and travels through Johto, thus she has no reason to meet Ash in Pallet Town.
My prediction is that at the end of the DP saga, Dawn will leave and head for Johto, Hoenn or Kanto (hopefully Kanto, so she can go to Pallet with Ash and Brock and meet Misty and Tracey) and Ash and Brock will go back to Kanto and have the finale reunion they always have at Pallet Town, with Misty, Gary and Tracey. Then maybe Ash will have a nostalgia moment and wonder what happened to May; Oak in response we'll say "she's fine, she just finished her Grand Festival and ended in the Top 8" or something like that.
But no, she won't appear at all (maybe through a videphone call, but not personally) because now she has nothing to do in Kanto, and as has said before, old characters usually are only brought back when necessary, and sometimes not even then (we're still waiting some closure for Misty's role) and seeing how Misty had no appearance at all in the DP saga (don't bring the lure, please, it was JUST A LURE and Ash didn't even said her name, she just refered vaguely to her as "an old friend of mine"), I don't see May having another appeareance in the anime, neither at the end of DP nor in 5Gen region/saga.
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