Annnnnnnnnd, with the revelation that the first episode of Smash in November will be dedicated to EP40 and will feature "The latest info on Eevee and its evolutions!" I am growing more and more confident Virgil will be the one to defeat Ash. He and his Pokemon are just getting so much emphasis.
How a battle that last 2 episodes could be a 1 vs 1? I expect a 3 vs 3 or better yet, a 4 vs 4 singles. I think that will be a ircular battle*.
In the manga scans we see Serperior hitting Pikachu with Dragon Tail. We know that in the games Dragon Tail force switches if there's other active pokemon remaining at the time.. With this, I think that the battle is:
Pikachu vs Serperior
Pikachu vs Serperior.
And Ash could win
*This means that the battle ends at the same manner than begins.
Welp! I'm sold. I sorta figured Virgil was gonna beat Ash anyway since he's the requisite guy-who-appears-just-before-the-League-and-beats-Ash, a tradition that hasn't been broken since the series began, but this news just makes it even more painfully obvious.
Hopefully Virgil's match against Ash will be as hilariously awkward and bad as Ash's battle with Tobias. If Ash is going to lose, I might as well get a good laugh from it.