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It's not about her age, it's about her narrative role. She's a mentor figure/final boss (in the games); her job isn't to keep improving and remaining on top forever but to eventually be surpassed as the protagonist comes into their own. That's what happens with champions in the games, but the...

Because she's not the main rival of this series. Same reason Paul constantly outdid Ash but Barry didn't. Edit: Also Iris was a major protagonist for three years and they'll want to show how she's improved. Alain likely got stomped because he wasn't a character with a large fanbase. Leon being...

I suspect the show has selectively ignored it since close to day one; Mikey in The Battling Eevee Brothers had one and he's rather significantly shorter than Ash so probably at least a few years younger. I imagine there's some specific set of rules regarding the whole thing, and it might just be...

That's Ash's job, I imagine. I promise you I have personally seen her lose in the games.;) Edit: Actually I think I read she lost to Cyrus in one of the manga but I could be wrong.