>>30990563Ash has literally, unironically, and absolutely never, ever won a league tournament and will never, ever win a league tournament until the anime ends. If it ever ends, that's it.
And in the anime, winning the league tournament is what allows you to challenge the E4 and the Champion. The Unnamed Kanto Fag did it, Jon Dickinson did it, Tyson and Tobias did it. Virgil and Alan declined because they were autists that didn't even care about the thing, but they had the chance to challenge it.
He has had the occasional unofficial battle against an E4, and he battled twice against Diantha in XY, but nothing official at all. And he never will.