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I would also expect the same of Alain. He doesn't look to have slacked off since the Kalos League and has even gotten a new Charizardite X. And Ash is using newer Pokémon who don't have the same experience as his older aces, most of who have battled in more than one region or league and even...

For Ash to look like he has a legitimate chance against Leon, assuming he's just using his Journeys Team and not his Reserves, I think that Cynthia has to at the very least beat Iris convincingly, if not outright curbstomp her. Leon trounced Alain, who managed to beat Ash with a Mega Pokémon...