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What about Camoron? Ash lost that one and that was at the LEAGUE, against a trainer who only brought along five Pokémon!

There can only be one though and it makes more sense for it to be Iris because she was a main character.

It seems unrealistic to me that Iris will lose in the first round, especially if it's against Lance. Iris is meant to be the best Dragon trainer, so why would she lose the first round? It goes against her dream if she's out before Lance. Obviously Ash will go against Alain and Leon will go...

I'm guessing the Masters 8 goes like this: Round 1: Ash vs. Cynthia Alain vs. Diantha Leon vs. Steven Iris vs. Lance Semi finals: Ash vs. Alain Iris vs. Leon Finals: Ash vs. Leon